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$222

4 BR / 3 BA / Sleeps 10

Marshall Haus - Chesapeake Bay vacation rentals
1 / 22

$222

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Marshall Haus

4 BR / 3 BA / Sleeps 10 | Quick view

Details

Marshall Haus Travel to a unique comfortably furnished round house in a secluded Caribbean paradise, featuring excellent snorkeling, fishing, and diving from a mile long white powder sand beach. Located in the vicinity of the quaint settlement of Current, Eleuthera population 130, an ideal getaway from the hustle and …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Parking
  • Grill
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$286

4 BR / 4 BA / Sleeps 8

Uhron 117151 - Chesapeake Bay vacation rentals
1 / 15

$286

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Uhron 117151

4 BR / 4 BA / Sleeps 8 | Quick view

Details

N/A
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$243

4 BR / 3 BA / Sleeps 10

3781- Rotella 51879 - Chesapeake Bay vacation rentals
1 / 14

$243

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3781- Rotella 51879

4 BR / 3 BA / Sleeps 10 | Quick view

Details

N/A
  • Shared outdoor pool (unheated)
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$343

5 BR / 3 BA / Sleeps 18

Bodenchak 112 36952 - Chesapeake Bay vacation rentals
1 / 1

$343

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Bodenchak 112 36952

5 BR / 3 BA / Sleeps 18 | Quick view

Details

N/A
  • Waterfront
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Fireplace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$500

3 BR / 2 BA / Sleeps 7

13067 Kruegle 97342 - Chesapeake Bay vacation rentals
1 / 20

$500

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13067 Kruegle 97342

3 BR / 2 BA / Sleeps 7 | Quick view

Details

2nd from the bay. Bay views from the raised first floor living room, kitchen, and main deck. Panoramic views of Barnegat bay from upper deck. Access to the ocean is one block away across Long Beach Blvd. Additional amenities include: coffee maker, virtual tour, private yard, furnished, 2 queen bed(s), 4 ceiling …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$250

4 BR / 3 BA / Sleeps 12

7 Reviews

$250

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Villa Wenona - Waterview Villa by Chesapeake Bay

4 BR / 3 BA / Sleeps 12 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

Property sleeps 10 with 4 bedrooms, 3 baths, living room, dining and sunroom. The majestic property of Villa Wenona sits on a beautiful lawn and wooded ¾ acre lot, yards from the Chesapeake Bay at the southern tip of Deal Island, MD. Enjoy exquisite sunsets from the comfortable sun room or the stunning balcony …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(7)

Very well equipped, clean, beautiful house and back yard includ

Left on Apr 15, 2013 for a stay in March 2013

We had a wonderful time. The owners are very friendly and prompt in responding with information to any question. The care takers next door are also very nice and helpful people. We will recommend this property to our friends any day!!!

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$450

3 BR / 3 BA / Sleeps 10

5 Reviews

$450

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Beautiful St. Michaels House Steps from Water and Town

3 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath, second floor has one …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(5)

Great Location, Great House, Great Time

Left on Jul 13, 2014 for a stay in July 2014

This house was perfect for a large family and very convenient for walking to sites in town. The house had a well equipped kitchen, nice backyard and barbecue grill. Within walking distance to local parks and public pool. We had nice holiday!

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$100

2 BR / 1 BA / Sleeps 4

1 / 8

$100

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316-DeFiore 35837

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Maxium occupancy = 4 people including babies, children & overnight guests. No smoking inside or outside of property. Additional amenities include: coffee maker, utilities included in season, furnished, 1 king bed(s), vacuum cleaner, cd player, smoke free, enclosed outside shower, gas heat, 2 single bed(s), pet free…
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$172

4 BR / 3 BA / Sleeps 8

1 / 26

$172

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2720-Stinson 41345

4 BR / 3 BA / Sleeps 8 | Quick view

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Nicely landscaped and multiple decks with this split level contemporary home. It sits on a large lot with the bay at the end of the street and the ocean at the other. The beach entrance is just across the blvd. This lovely home feautures 4 large bedrooms and 2 1/2 baths with the master bdr having it s own. Plenty of …
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$175

3 BR / 2 BA / Sleeps 6

3 Reviews

$175

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Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina on Knapps Narrows. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Relaxing weekend stay

Left on Mar 08, 2014 for a stay in March 2014

My husband and I spent a weekend at the Roost on Tilghman Island and it was so relaxing. We were really able to unplug and I slept better in their loft bedroom than I had in my own bed in weeks. The cottage was really sweet- it looks small on the outside but it's actually very spacious and I love how it was decorated. Everything was spotless and in good working order. We enjoyed the sun room/…

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$375

4 BR / 3 BA / Sleeps 10

1 Reviews

$375

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Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and furnished for a comfortable …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Perfect weekend getaway!

Left on Jan 10, 2014 for a stay in December 2013

My family recently spent a memorable weekend in December at Sandy Pines. We comfortably shared the house with a group of friends -- three other couples and their young children. The house has a lovely home-away-from-home feel. We especially enjoyed the wood-burning fireplace in the evenings.
Sandy Pines is perfectly situated -- a short drive from St. Michaels, and on a tranquil spot by the Bay…

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$500

6 BR / 3 BA / Sleeps 18

6 Reviews

$500

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Chesapeake Bay Waterfront, Private Dock, Beach

6 BR / 3 BA / Sleeps 18 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

The Swan's Nest in Cambridge, Maryland, has all that the Chesapeake Bay has to offer: sun, sand, fishing, crabbing, a par 3 golf course on site and so much more. The spacious and lovingly restored farmhouse can accommodate 18 guests. The kitchen is fully equipped and a barbeque pit is just outside on the patio. …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Fantastic Bay Experience!

Left on Jul 16, 2012 for a stay in July 2012

My extended family (12 plus part week guests) just got back from a week at Swan's Nest. Hap was a fantastic host and tried really hard to ensure we had what we needed for the needs and interests of our group. I can't say enough about his personal involvement and patience in answering our questions.

It was a fantastic experience - we went crabbing - a lot - we brought supplies to run a trot …

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$125

2 BR / 1 BA / Sleeps 6

1 / 21

$125

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Captain's Watch Vacation Cottage

2 BR / 1 BA / Sleeps 6 | Quick view

Details

Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on the Eastern Shore. …
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

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    $250

    3 BR / 2 BA / Sleeps 10

    1 / 10

    $250

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    Shelwood Baie

    3 BR / 2 BA / Sleeps 10 | Quick view

    Details

    North Beach, known as "The Jewel of the Chesapeake", is a small bayside town with a village feel. There is a fabulous farmers market on Friday evenings starting in April, shops and restaurants to explore, wine tastings, an art gallery, a boardwalk perfect for a stroll along the beach, bicycles for rent, a …
    • Wireless Internet
    • Outdoor Dining Area
    • A/C or climate control
    • Central heating
    • Balcony or terrace
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask

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    $159

    3 BR / 2 BA / Sleeps 5

    1 / 15

    $159

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    Best kept secret by the bay

    3 BR / 2 BA / Sleeps 5 | Quick view

    Details

    Hooper's Island is located between the Honga River and Chesapeake Bay on Marylands Eastern Shore. This unique island is a "MUST DO" on your bucket list. Especially noted for: Maryland's famous Blue Crabs and Breathtaking Sunsets!!! April thru October on Hooper's Island is must do on your bucket list …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Suitable for children - ask

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    $164

    3 BR / 2 BA / Sleeps 8

    1 / 49

    $164

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    Fun DC/Annaoplis Chesapeake Waterfront Cottge

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    This 3 bedroom/2 bath cottage is just the spot for a get-away with other couples or your entire family! Nestled on 2 country-like acres in a surprisingly convenient corner of the Chesapeake Bay, this unique area is just over 20 minutes south of Annapolis and 45 minutes from Wash DC, Alexandria VA, or Baltimore. …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Washing Machine
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $250

    4 BR / 3 BA / Sleeps 10

    1 / 12

    $250

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    Million dollar view on the Chesapeake

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    Fredelig sted"(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine and birch wood inside. The bright panoramic view of the Chesapeake from the great room, master bedroom or deck elicits a relaxed, peaceful mood as soon as you arrive. Watch the seagulls or osprey …
    • Waterfront
    • A/C or climate control
    • Porch
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $225

    4 BR / 2 BA / Sleeps 9

    1 Reviews

    $225

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    Cobb Island Waterfront Home with Beach & Dock

    4 BR / 2 BA / Sleeps 9 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Welcome to our Cobb Island, Maryland Home, on the waterfront in Southern Maryland, one hour from Washington D.C. - the perfect spot to spend your next relaxed family vacation enjoying water oriented activities and fabulous river views. We have been renting this house to more than 200 families since 1999 and have many…
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Great Waterfront Rental for families and groups of friends

    Left on Dec 28, 2011 for a stay in July 2010

    I only have great things to say about Ed Mullan's Cobb Island rental.
    Having stayed there for several weekends, I can attest to the
    comfortable and well-appointed house, fantastic location close to
    Washington, DC, and abundance of fun activities at the house and
    surrounding area. The property is ideal for families as well as groups of friends. Both the indoor and outdoor areas are conducive for …

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    $100

    3 BR / 2 BA / Sleeps 6

    1 / 25

    $100

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    SPECTACULAR WATERFRONT 3BR CONDO-CRISFIELD ,MD

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Relax & Enjoy!! You May Not Want to Leave. The Harbour Light Condominiums are the Waterfront Jewel of Crisfield. This unit is situated direct waterfront and faces due west toward the bay. A better sunset view cannot be found. You'll enjoy the sunsets, the wildlife, boat watching, and the overall peaceful …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $250

    3 BR / 2 BA / Sleeps 6

    1 / 9

    $250

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    Renovated Luxury Waterview House

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to beach, boardwalk, …
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children

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    $225

    3 BR / 3 BA / Sleeps 7

    1 / 18

    $225

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    My Seaside Cottage and La Petite Maison

    3 BR / 3 BA / Sleeps 7 | Quick view

    Details

    My Seaside Cottage and La Petite Maison Located on beautiful, secluded North Beach of Current, Eleuthera, our 2-bedroom cottage is situated in the vicinity of the quaint settlement of Current, Eleuthera population 130, an ideal getaway from the hustle and bustle of 21st Century living. A 10 minute drive to the ferry …
    • Waterfront
    • Parking
    • Grill
    • Towels Provided
    • Microwave
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $125

    1 BR / 1 BA / Sleeps 3

    2 Reviews

    $125

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    Hoopers Island Studio, 360 Degrees WATER VIEWS

    1 BR / 1 BA / Sleeps 3 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    GRAND OPENING Spring 2014: 360 Degree Views, WATERFRONT (Honga River) and WATERBACK (Chesapeake Bay)! Scenic, peaceful and spacious 1 bedroom/studio apartment located on the entire second floor of our property. Available for 3 night minimum stays ($350 per 3 night stay), please inquire about discounted weekly …
    • Waterfront
    • Ocean or water views
    • Fireplace
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children - ask

    Details

    Reviews

    (2)

    What a fantastic stay!

    Left on Jun 09, 2014 for a stay in May 2014

    As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons.

    Inside the house, we found all that we could need and more. The décor was adorable, though both aesthetically and functionally vintage. We found a very thoughtful welcome bag and bottle of wine on the dining table as soon …

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    $110

    1 BR / 1 BA / Sleeps 4

    2 Reviews

    $110

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    Bayview by Chesapeake Bay

    1 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    This cozy one-bedroom house is a wonderful spot for a weekend getaway or as a base to discover the culture, history and cuisine of Maryland's Eastern Shore. Enjoy nature, birds - bald eagles, ospreys, blue herons - stunning sunsets and more by the bay. The one-bedroom house includes full kitchen, living room, bedroom…
    • Ocean or water views
    • Internet Access
    • Outdoor Dining Area
    • A/C or climate control
    • Patio
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Bayview cottage

    Left on Jun 09, 2014 for a stay in June 2014

    I stayed at Francesca's lovely Bayview cottage on the Chesapeake Bay in Tolchester, Maryland this weekend. The cottage is delightful, with porches on three sides, comfy beds, and a well appointed kitchen. After sleeping soundly, we awoke to the sight and sounds of songbirds in the yard and eagles, herons, and osprey flying over the Bay. Francesca is the perfect hostess!

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    $759

    6 BR / 6 BA / Sleeps 12

    1 / 38

    $759

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    BayCottage Waterfront Vacation Retreat St.Michaels

    6 BR / 6 BA / Sleeps 12 | Quick view

    Details

    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are 6 bedrooms, 5.5 …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $100

    1 BR / 1 BA / Sleeps 5

    5 Reviews

    $100

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    1 bedroom cottage near water, dog friendly

    1 BR / 1 BA / Sleeps 5 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch with day bed, a full kitchen, and a backyard …
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Quiet and peaceful!

    Left on Sep 26, 2011 for a stay in September 2011

    We had a very nice stay at Seahorse cottage. It was on a quiet street, but only a short walk to the boardwalk. The owners are wonderful to talk to. We hope to go back next year for our anniversary.

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    $145

    3 BR / 1 BA / Sleeps 7

    1 Reviews

    $145

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    Chester River House with Views

    3 BR / 1 BA / Sleeps 7 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at Washington College in…
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    A PLEASANT STAY

    Left on Aug 29, 2014 for a stay in August 2014

    what a beautiful area of md. to stay at for an relaxing get away.the beautiful sun sets and sunrise.

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    $150

    2 BR / 1 BA / Sleeps 6

    1 / 22

    $150

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    Chesapeake Bay Sunrises AND Sunsets

    2 BR / 1 BA / Sleeps 6 | Quick view

    Details

    Located in Frenchtown, MD, 30 min south of Salisbury, MD on Chesapeake Bay's Eastern Shore. This is a private home on an island in the middle of ten thousand acres of salt marsh and near a national wildlife management area. Views from the bedroom, enjoy waterfront sunrises, water views from the living room & …
    • Waterfront
    • Ocean or water views
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly

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    $295

    3 BR / 3 BA / Sleeps 8

    3 Reviews

    $295

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    Retreat at a quiet, water front cottage

    3 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 3 Reviews

    Details

    Reviews

    (3)

    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent County area. This south …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Fireplace
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (3)

    Construction in progress and mud everywhere.

    Left on Oct 18, 2014 for a stay in October 2014

    If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.

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    $280

    4 BR / 2 BA / Sleeps 8

    2 Reviews

    $280

    Inquire

    Peaceful, Waterfront Home w/Pier on Kent Island

    4 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The location is serene on a 3 …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Unbelievable value

    Left on Nov 04, 2010 for a stay in May 2010

    We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we…

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    $190

    3 BR / 1 BA / Sleeps 5

    1 / 41

    $190

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    "The Cottage" Cambridge Chesapeake Waterfront Home

    3 BR / 1 BA / Sleeps 5 | Quick view

    Details

    "The Cottage" at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch or soak in the 450 gallon hot tub. Fish and …
    • Waterfront
    • Hot Tub/Jacuzzi
    • A/C or climate control
    • Central heating
    • Deck
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $95

    1 BR / 1 BA / Sleeps 4

    5 Reviews

    $95

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    Charming Apartment in Historic Chestertown, MD

    1 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An air mattress can be set up in the living room for 2 additional guests. An outdoor deck with cafe table and chairs is a …
    • Waterfront
    • Internet Access
    • Outdoor Dining Area
    • A/C or climate control
    • Central heating

    Details

    Reviews

    (5)

    Cute little apartment right in Chestertiwn.

    Left on Jun 05, 2014 for a stay in May 2014

    The apartment in Chestertown is super cute and convenient. Walking distance to the water and all the cute cafés and restaurants. Clean and simple with a cute little balcony. The place was great and the hosts were helpful and responsive.

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    $249

    2 BR / 2 BA / Sleeps 5

    1 / 17

    $249

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    Chesapeake Bay House

    2 BR / 2 BA / Sleeps 5 | Quick view

    Details

    Outstandingly beautiful and immaculately maintained light-filled custom-built home with stunning, unobstructed views of the wonderful Chesapeake Bay in the picturesque town of North Beach. Steps away from the boardwalk in front of the bay. Within a 45-min drive from Washington DC (just 33 miles), Baltimore & Annapolis…
    • Waterfront
    • Hot Tub/Jacuzzi
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

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    $450

    3 BR / 3 BA / Sleeps 8

    1 / 18

    $450

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    Historic Waterfront Property with Wi-Fi and Dock

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed with 2 twins beds and a…
    • Waterfront
    • Wireless Internet
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children

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    $375

    4 BR / 4 BA / Sleeps 10

    1 / 37

    $375

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    Luxury vacation condominum with private beach

    4 BR / 4 BA / Sleeps 10 | Quick view

    Details

    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen size bed for the 4…
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $125

    2 BR / 2 BA / Sleeps 5

    1 / 11

    $125

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    Chesapeake bay vacation home

    2 BR / 2 BA / Sleeps 5 | Quick view

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    Condo on first fairway of Chesapeake Bay Golf Club, North East. Excellent vacation home for golfers, hikers, any kind of water sports. Elk Neck State Forest with a shooting range and miles of hiking trails less than 3 miles away. North East River, Susquehanna River, Bohemia River, Elk Neck River and Sassafrass …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Central heating
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible

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    $449

    6 BR / 5 BA / Sleeps 16

    9 Reviews

    $449

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    Stunning, Newer Chesapeake Waterfront Rental

    6 BR / 5 BA / Sleeps 16 | Quick view
    “ Excellent ” 9 Reviews

    Details

    Reviews

    (9)

    Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge, Easton, Oxford & St. …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Sauna
    • Internet Access
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (9)

    GREAT Vacation!

    Left on May 05, 2009 for a stay in August 2008

    We really had a GREAT stay. The house is much more than we expected; it's very well done and comfortable (the owner was nice as well). The water views are amazing and the grounds perfect. We swam, fished, crabbed, biked and boated - had a great time off property as well. This was a TOP notch vacation.- thanks!

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    $360

    7 BR / 4 BA / Sleeps 11

    2 Reviews

    $360

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    Large Historic Home On Harbor in St. Michaels

    7 BR / 4 BA / Sleeps 11 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and shops in St. …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    This was the perfect home for a week of wedding planning and family relaxation time.

    Left on Jul 23, 2014 for a stay in June 2014

    Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time together finalizing wedding plans. The stay at the Harrison Home added so many memories to the already fond memories of a wedding. We cooked together with all the amenities in the kitchen. The home was so large we could …

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    $710

    3 BR / 2 BA / Sleeps 9

    3 Reviews

    $710

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    CEDAR POINT

    3 BR / 2 BA / Sleeps 9 | Quick view
    “ Excellent ” 3 Reviews

    Details

    Reviews

    (3)

    This charming waterfront cottage on 6.5 private acres sits among swans and eagles on Marylands beautiful Eastern Shore. This professionally decorated cottage is packed with modern ammenities and charm. Waterfront Pool, Dock with seating boat slip with and water and electric; 1 canoe and 3 two person kayaks, …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (3)

    A Vacation to Remember

    Left on Apr 25, 2011 for a stay in September 2010

    My kids still talk about it...It was the best Vacation they have had...We traveled to Europe many times but this is the week they will remember..Thank you for making this a memorable vacation..We will be back!!!

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    $375

    2 BR / 1 BA / Sleeps 6

    1 Reviews

    $375

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    Cottage 2 at Grandview Pleasure Point

    2 BR / 1 BA / Sleeps 6 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces, air …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Outdoor Dining Area
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Wonderful!

    Left on Sep 30, 2013 for a stay in September 2013

    Our family has been vacationing at Grandview for over 20 years. I think that says it all. Beautiful location, gorgeous sunsets, peaceful and quite. Serene. Plenty of crabbing, swimming, fishing and just plan relaxing. The cottages are nicely furnished, cozy, clean and well-stocked kitchen. Plenty to do in the area-close to St. Michaels, hiking, cycling, nice restaurants. We love it here.

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    $1,200

    5 BR / 4 BA / Sleeps 18

    2 Reviews

    $1,200

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    Yr Round Waterfront Home w/ Dock & Pool - Slps 18

    5 BR / 4 BA / Sleeps 18 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Swan Cove awaits your family vacation or group! It's also an ideal place for a most memorable wedding. This incredible, newly redesigned waterfront home with a private dock offers spectacular views with a large swimming pool, 4 kayaks, outdoor firepit (firewood is furnished), playground and a large outdoor grill. The …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Dream vacation

    Left on Oct 18, 2012 for a stay in August 2012

    We spent a week a Swan cove. the entire Family loved the house. Very spacious, clean and the kids had a blast in the pool. Great setting with the private dock, fire pit, playground just an amazing home.
    We already reserved for next year!!!

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    $195

    2 BR / 2 BA / Sleeps 4

    1 Reviews

    $195

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    Premier Cottage in St. Michaels- In Town Location!

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor. The first floor of the…
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    I will never go back to the Jersey Shore Again!!!

    Left on Aug 18, 2014 for a stay in August 2014

    Location location location!

    Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!

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    $250

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $250

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    Unique, Affordable Nature-Oriented Getaway Home

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Average ” 1 Reviews

    Details

    Reviews

    (1)

    Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide covered front porch and …
      • Pet friendly
      • Smoking allowed - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Nice house but it is not on the water

      Left on Oct 26, 2012 for a stay in July 2012

      This is a lovely older house with lots of room for families. We are very grateful that she accepts dogs and even better that the house is so clean you can't tell that dogs have stayed there. The electronics are a bit old but useable and there is no wifi. There are bikes available for use and the area would be great for bike riding but in July when we were there it was over 100 every day and …

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      $1,100

      7 BR / 6 BA / Sleeps 28

      5 Reviews

      $1,100

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      Yr Round Estate on Bay / Family Reunions Sleeps 28

      7 BR / 6 BA / Sleeps 28 | Quick view
      “ Excellent ” 5 Reviews

      Details

      Reviews

      (5)

      Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates up to 28 people and …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (5)

      Great hospitality...

      Left on Apr 24, 2012 for a stay in April 2012

      The house is well decorated and spacious, fantastic for family gatherings. We had a great experience that will be remembered for the rest of our lives.

      This property had all you needed for a great family vacation, but above all, the owner is a master of hospitality - he was very accommodating to every request we had.

      I hope to go back to this house for another week soon.

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      $190

      2 BR / 2 BA / Sleeps 5

      12 Reviews

      $190

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      Location Location! St Michaels-- In Town Cottage!

      2 BR / 2 BA / Sleeps 5 | Quick view
      “ Excellent ” 12 Reviews

      Details

      Reviews

      (12)

      The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Washing Machine
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask

      Details

      Reviews

      (12)

      Crabtastic Great Escape

      Left on Aug 26, 2011 for a stay in August 2011

      This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable.

      I have visited this cottage several…

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      $449

      7 BR / 5 BA / Sleeps 18

      11 Reviews

      $449

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      Waterfront Chespeake Bay Retreat

      7 BR / 5 BA / Sleeps 18 | Quick view
      “ Excellent ” 11 Reviews

      Details

      Reviews

      (11)

      New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal for large family …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (11)

      Wondeful home - Great for Fishing!

      Left on May 04, 2009 for a stay in April 2009

      We had an amazing week at this gorgeous house. The house is brand new and immaculate. Everything in it is brand new!! It truly felt like home. The owners are amazing - it was a warmer week than expected and they went out of their way to open the pool for us. They also gave a lot of great recommendations on places to eat. We took out the boat and the kids had a great time fishing and …

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      $665

      4 BR / 3 BA / Sleeps 13

      8 Reviews

      $665

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      Grandview Mainhouse

      4 BR / 3 BA / Sleeps 13 | Quick view
      “ Excellent ” 8 Reviews

      Details

      Reviews

      (8)

      Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (8)

      relaxing

      Left on Jun 24, 2011 for a stay in September 2010

      A secret hideaway! We had never been to St. Michael's and even though this is out of town we like privacy. We stayed in one of the smaller units and it was perfect. Clean and updated with beautiful finishes. Would have loved to have a motor on the boat though!

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      $280

      3 BR / 3 BA / Sleeps 6

      1 / 9

      $280

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      RESTORED WATERFRONT COTTAGE

      3 BR / 3 BA / Sleeps 6 | Quick view

      Details

      You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round vacationing. Our …
      • Waterfront
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $250

      2 BR / 2 BA / Sleeps 6

      1 / 10

      $250

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      Relaxation At Its Best!!!!

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Come vacation in this brand-new home in beautiful Elk Neck and you will be glad you did! It is definitely a most gorgeous location and very peaceful, set back in the woods along the river. Elk Neck is approximately eight miles south of the town of North East, MD where there are many neat little shoppes and fabulous …
      • Waterfront
      • Ocean or water views
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Suitable for children
      • Suitable for the elderly - ask

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      $575

      4 BR / 4 BA / Sleeps 8

      1 / 4

      $575

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      Red Point Lighthouse

      4 BR / 4 BA / Sleeps 8 | Quick view

      Details

      Custom lighthouse with 4 bedrooms and 4 baths overlooking the Chesapeake Bay. Within one hour from Baltimore, MD, Wilmington DE, and Lancaster, PA. Perfect for large families, weddings, ect.
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Fireplace
      • Washing Machine
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

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      $250

      1 BR / 2 BA / Sleeps 3

      1 Reviews

      $250

      Book

      Tilghman Landing

      1 BR / 2 BA / Sleeps 3 | Quick view
      “ Excellent ” 1 Reviews

      Details

      Reviews

      (1)

      Watch the dazzling sunsets over the bay. Choose from our one bedroom Waterfront Cottages located on the Chesapeake Bay side of Tilghman Island: It is a beautiful 2-story one bedroom cottage with stunning views of the bay from the 2nd floor bedroom, with hardwood floors throughout, a full kitchen, satellite TV, DVD …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Outdoor Dining Area
      • A/C or climate control
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (1)

      Get away weekend with friends

      Left on Jul 17, 2014 for a stay in June 2014

      Have stayed here two times. Once in the 2 bedroom and once in the one bedroom. Both facilities are clean and welcoming. Both properties provide beautiful views and easy access to the docks and bay. The owners are very nice and also host a fun crab feast on Saturday evenings.

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