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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

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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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$225

4 BR / 3 BA / Sleeps 12

7 Reviews

$225

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Villa Wenona - Waterview Villa by Chesapeake Bay

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

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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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$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

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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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$250

4 BR / 3 BA / Sleeps 10

Million dollar view on the Chesapeake - Chesapeake Bay vacation rentals
1 / 12

$250

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Million dollar view on the Chesapeake

4 BR / 3 BA / Sleeps 10 | Quick view

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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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$75

2 BR / 1 BA / Sleeps 6

Captain's Watch Vacation Cottage - Chesapeake Bay vacation rentals
1 / 21

$75

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Captain's Watch Vacation Cottage

2 BR / 1 BA / Sleeps 6 | Quick view

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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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$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

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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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$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

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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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$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

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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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$180

4 BR / 2 BA / Sleeps 8

2 Reviews

$180

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Peaceful, Waterfront Home w/Pier on Kent Island

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

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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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$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

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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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$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

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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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$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

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"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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$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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$150

3 BR / 2 BA / Sleeps 6

1 / 9

$150

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Renovated Luxury Waterview House

3 BR / 2 BA / Sleeps 6 | Quick view

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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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$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

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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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$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

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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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$160

2 BR / 2 BA / Sleeps 4

1 Reviews

$160

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Premier Cottage in St. Michaels

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

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Reviews

(1)

The historic Thomas Blades House is a 2 bedroom, 2 bathroom vacation cottage that is a short walk from all museums, parks, restaurants, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor. The first floor of the original portion of the Blades House includes a …
  • 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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$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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$290

7 BR / 4 BA / Sleeps 11

2 Reviews

$290

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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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$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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$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

Details

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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$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

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

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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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