Showing

PreviousNext property

$90

3 BR / 3 BA / Sleeps 6

2 Reviews

$90

Book

Waterfront Vacation Room Rentals

Trappe house – 15.6 mi away
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Beautiful, serene waterfront home on the Chesapeake Bay. One hour from the Atlantic Ocean (Ocean City, Assateague Island) and Annapolis, One and a half hours from Washington DC and Baltimore. Many nearby places worth visiting, including picturesque St. Michaels and the Blackwater Wildlife Refuge (home of the bald …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Dimitri is an unbelievable host! There wasn't any stone he left unturnrned in order to provide us w

Left on Aug 14, 2014 for a stay in August 2014

Our stay was incredible!! The house was spotless and offered every convience one could want! If it wasn't there all you had to do was ask for it and he provided it or informed you where you could get it!

Our stay was really disjointed by this weeks Bad Storm! But the Chesepeake Bay side home weathered it relentlessly. Only to have a beautiful week to look forward to!

PreviousNext property

$800

3 BR / 3 BA / Sleeps 10

1 Reviews

$800

Book

Beautifully water front Contemporary Home in Bay R

Annapolis house – 17.0 mi away
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Bright, open, waterfront contemporary located on a landscaped property with magnificent views of Lake Ogleton! Pier (4'MLW) for your boat, crabbing, fishing and swimming. Bay Ridge Subdivison has great views, sandy beaches, streets for jogging, nature walks, and just great places to chill. Once you see the view from…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful Family House!

Left on Oct 17, 2013 for a stay in August 2013

We were fortunate to stay in this lovely home over Plebe Parent Weekend. It was perfect for our family of 6. There was plenty of room to spread out or come together for family time. The large dining table made us feel right at home. The bedding was fresh with new linens and towels in all the rooms. We enjoyed the lovely water views and great location. The Bay Ridge house is a short ride to the …

PreviousNext property

$150

1 BR / 1 BA / Sleeps 5

5 Reviews

$150

Inquire

1 bedroom cottage near water, dog friendly

North Beach cottage – 16.6 mi away
1 BR / 1 BA / Sleeps 5 | Quick view
Excellent5 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.

PreviousNext property

$375

4 BR / 3 BA / Sleeps 10

1 Reviews

$375

Book

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

Saint Michaels house
4 BR / 3 BA / Sleeps 10 | Quick view
Excellent1 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…

PreviousNext property

$250

3 BR / 2 BA / Sleeps 6

Renovated Luxury Waterview House - Saint Michaels vacation rentals
1 / 9

$250

Book

Renovated Luxury Waterview House

North Beach house – 16.3 mi away
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

PreviousNext property

$175

3 BR / 2 BA / Sleeps 6

3 Reviews

$175

Book

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

Tilghman cottage – 6.1 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 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/…

PreviousNext property

$190

2 BR / 2 BA / Sleeps 4

1 Reviews

$190

Inquire

Premier Cottage in St. Michaels- In Town Location!

Saint Michaels house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent1 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!

PreviousNext property

$350

7 BR / 4 BA / Sleeps 11

2 Reviews

$350

Inquire

Large Historic Home On Harbor in St. Michaels

Saint Michaels house
7 BR / 4 BA / Sleeps 11 | Quick view
Excellent2 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 …

PreviousNext property

$280

4 BR / 2 BA / Sleeps 8

2 Reviews

$280

Inquire

Peaceful, Waterfront Home w/Pier on Kent Island

Chester house – 13.3 mi away
4 BR / 2 BA / Sleeps 8 | Quick view
Excellent2 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…

PreviousNext property

$449

7 BR / 5 BA / Sleeps 18

11 Reviews

$449

Inquire

Waterfront Chespeake Bay Retreat

Cambridge house – 11.6 mi away
7 BR / 5 BA / Sleeps 18 | Quick view
Excellent11 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 …

PreviousNext property

$1,200

5 BR / 4 BA / Sleeps 18

2 Reviews

$1,200

Inquire

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

Cambridge house – 14.2 mi away
5 BR / 4 BA / Sleeps 18 | Quick view
Excellent2 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!!!

PreviousNext property

$1,100

7 BR / 6 BA / Sleeps 28

5 Reviews

$1,100

Inquire

Yr Round Estate on Bay / Family Reunions Sleeps 28

Cambridge villa – 15.4 mi away
7 BR / 6 BA / Sleeps 28 | Quick view
Excellent5 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.

PreviousNext property

$449

6 BR / 5 BA / Sleeps 16

9 Reviews

$449

Inquire

Stunning, Newer Chesapeake Waterfront Rental

Cambridge house – 16.2 mi away
6 BR / 5 BA / Sleeps 16 | Quick view
Excellent9 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!

PreviousNext property

$375

2 BR / 1 BA / Sleeps 6

1 Reviews

$375

Inquire

Cottage 2 at Grandview Pleasure Point

Bozman house – 3.7 mi away
2 BR / 1 BA / Sleeps 6 | Quick view
Excellent1 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.

PreviousNext property

$665

4 BR / 3 BA / Sleeps 13

8 Reviews

$665

Inquire

Grandview Mainhouse

Bozman house – 3.7 mi away
4 BR / 3 BA / Sleeps 13 | Quick view
Excellent8 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!

PreviousNext property

$500

6 BR / 3 BA / Sleeps 18

6 Reviews

$500

Inquire

Chesapeake Bay Waterfront, Private Dock, Beach

Cambridge house – 16.2 mi away
6 BR / 3 BA / Sleeps 18 | Quick view
Excellent6 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 …

PreviousNext property

$209

2 BR / 1 BA / Sleeps 6

1 / 11

$209

Book

Love Point Bay Vacation Home

Stevensville condo – 17.6 mi away
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave your worries behind …
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    PreviousNext property

    $164

    3 BR / 2 BA / Sleeps 8

    1 / 49

    $164

    Book

    Fun DC/Annaoplis Chesapeake Waterfront Cottge

    Deale bungalow – 15.9 mi away
    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

    PreviousNext property

    $450

    3 BR / 3 BA / Sleeps 10

    5 Reviews

    $450

    Book

    Beautiful St. Michaels House Steps from Water and Town

    Saint Michaels house
    3 BR / 3 BA / Sleeps 10 | Quick view
    Excellent5 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!

    PreviousNext property

    $250

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $250

    Book

    Unique, Affordable Nature-Oriented Getaway Home

    Cambridge house – 12.1 mi away
    3 BR / 2 BA / Sleeps 6 | Quick view
    Average1 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 …

      PreviousNext property

      $710

      3 BR / 2 BA / Sleeps 9

      3 Reviews

      $710

      Inquire

      CEDAR POINT

      Church Creek house – 17.9 mi away
      3 BR / 2 BA / Sleeps 9 | Quick view
      Excellent3 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!!!

      PreviousNext property

      $250

      2 BR / 1 BA / Sleeps 4

      1 / 12

      $250

      Book

      2 Bedroom Unique Private Waterfront Escape

      Easton condo – 4.8 mi away
      2 BR / 1 BA / Sleeps 4 | Quick view

      Details

      Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to offer! The …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer

      PreviousNext property

      $595

      5 BR / 3 BA / Sleeps 20

      1 / 26

      $595

      Book

      Annapolis Crows Nest Cottage: Chesapeake Bay View

      Annapolis villa – 15.9 mi away
      5 BR / 3 BA / Sleeps 20 | Quick view

      Details

      Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden level, spa inspired …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly

      PreviousNext property

      $500

      8 BR / 6 BA / Sleeps 16

      1 / 29

      $500

      Inquire

      Maryland Eastern Shore Waterfront Estate

      Trappe villa – 10.4 mi away
      8 BR / 6 BA / Sleeps 16 | Quick view

      Details

      Martins Point is a late 18th Century house and cottages on Maryland's historic Eastern Shore where the Underground Railroad once passed through the property. It is located on a secluded finger of land, surrounded by water on three sides, a place to unwind, immerse yourself in the natural beauty of the Chesapeake Bay …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - elevator access

      PreviousNext property

      $180

      2 BR / 2 BA / Sleeps 5

      12 Reviews

      $180

      Inquire

      Location Location! St Michaels-- In Town Cottage!

      Saint Michaels house
      2 BR / 2 BA / Sleeps 5 | Quick view
      Excellent12 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…

      PreviousNext property

      $250

      3 BR / 4 BA / Sleeps 8

      1 Reviews

      $250

      Inquire

      ENDLESS SUNSETS - The perfect getaway!

      Claiborne house – 5.4 mi away
      3 BR / 4 BA / Sleeps 8 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake Bay. Every bedroom …
      • Waterfront
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Hard to find and worth the effort

      Left on Oct 10, 2014 for a stay in September 2014

      Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and bathrooms galore. The only nitpick I have is the wifi seemed to fade in and out kicking us off regularly.

      But with such a great view and wonderful sunsets - you won't want to be on wifi anyway.

      Be sure to get good …

      PreviousNext property

      $250

      4 BR / 3 BA / Sleeps 8

      1 / 17

      $250

      Book

      Chez Cinquai

      Tilghman house – 6.0 mi away
      4 BR / 3 BA / Sleeps 8 | Quick view

      Details

      Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet kitchen, custom wood …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask

      PreviousNext property

      $759

      6 BR / 6 BA / Sleeps 12

      1 / 38

      $759

      Book

      BayCottage Waterfront Vacation Retreat St.Michaels

      Saint Michaels villa
      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

      PreviousNext property

      $1,500

      0 BR / 4 BA / Sleeps 6

      1 / 7

      $1,500

      Book

      Eastern Shore Vacation Rental

      Oxford house – 8.4 mi away
      0 BR / 4 BA / Sleeps 6 | Quick view

      Details

      Secluded, tranquil home located on the water, between Easton and Oxford, Maryland. Includes five bedrooms, four bathrooms, fully equipped kitchen, sun porch, swimming pool and tennis courts. Grounds include private driveway, miles of walking paths, and dock with two kayaks.
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $450

      3 BR / 3 BA / Sleeps 8

      1 / 18

      $450

      Book

      Historic Waterfront Property with Wi-Fi and Dock

      Saint Michaels house
      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

      PreviousNext property

      $575

      4 BR / 4 BA / Sleeps 14

      1 / 23

      $575

      Inquire

      Chesapeake Bay Spectacular

      Stevensville house – 9.4 mi away
      4 BR / 4 BA / Sleeps 14 | Quick view

      Details

      Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes complete with …
      • Waterfront
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Washing Machine
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $450

      4 BR / 3 BA / Sleeps 10

      1 / 12

      $450

      Inquire

      Chesapeake Bay Luxury Vacation Home, 5 Star

      Grasonville house – 14.6 mi away
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other accommodations do not. For large…
      • Waterfront
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Washing Machine
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $250

      2 BR / 2 BA / Sleeps 4

      1 / 8

      $250

      Book

      Waterfront Boat Vacation Rental

      Davidsonville houseboat – 15.1 mi away
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      2 bedroom, 2 bath with living salon, kitchen, and an aft deck
      • Waterfront
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Sauna
      • Internet Access
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $257

      4 BR / 3 BA / Sleeps 10

      1 / 17

      $257

      Inquire

      KI Golf House:A Par for the Course&Mile from Beach

      Kent Island house – 12.0 mi away
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      LOCATION…STAYCATION…GOLFCATION…right on Kent Island! KI Golf House: A Par for the Course Less than a mile to Dirty Dave's a gorgeous little beach and tiki bar. A short walk to the Chesapeake Bay. Call/email Donna and book it today! KI Golf House offers 4 Bedrooms, 2 ½ Baths, an open Kitchen Dining area…
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $280

      3 BR / 3 BA / Sleeps 6

      1 / 9

      $280

      Inquire

      RESTORED WATERFRONT COTTAGE

      Saint Michaels 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

      PreviousNext property

      $375

      4 BR / 4 BA / Sleeps 10

      1 / 37

      $375

      Inquire

      Luxury vacation condominum with private beach

      Chester house – 14.4 mi away
      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

      PreviousNext property

      $250

      4 BR / 3 BA / Sleeps 10

      1 / 12

      $250

      Inquire

      Million dollar view on the Chesapeake

      Deale house – 16.8 mi away
      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

      PreviousNext property

      $190

      3 BR / 1 BA / Sleeps 5

      1 / 41

      $190

      Inquire

      "The Cottage" Cambridge Chesapeake Waterfront Home

      Cambridge cottage – 13.4 mi away
      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

      PreviousNext property

      Inquire for rates.

      2 BR / 1 BA / Sleeps 4

      1 / 16

      Inquire for rates

      Inquire

      204 Shipping Creek Dr.

      Stevensville house – 12.1 mi away
      2 BR / 1 BA / Sleeps 4 | Quick view

      Details

      This lovely cottage hideaway, inlaw suite is in the tree tops above a three car extended garage. Lovingly appointed with twin tester beds in one bedroom and a queen in the master. It has many lovely antique pieces,inhereted from relatives. An in ground poolwelcomes you and the warmseasons. Situated on a tip of Kent …
      • Shared outdoor pool (unheated)
      • A/C or climate control
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      Inquire for rates.

      3 BR / 3 BA / Sleeps 8

      1 / 23

      Inquire for rates

      Inquire

      2 Upshur Ave

      Annapolis house – 16.7 mi away
      3 BR / 3 BA / Sleeps 8 | Quick view

      Details

      N/A
      • Shared outdoor pool (unheated)
      • Fireplace
      • A/C or climate control
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      Inquire for rates.

      4 BR / 4 BA / Sleeps 10

      1 / 1

      Inquire for rates

      Inquire

      916 Langdon Court

      Annapolis house – 19.0 mi away
      4 BR / 4 BA / Sleeps 10 | Quick view

      Details

      N/A
      • Fireplace
      • A/C or climate control
      • Balcony or terrace
      • Parking
      • Grill
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Looking for more rentals?


      We're showing only results that match your dates and preferences.


      See all 60 Saint Michaels rentals, all 39 Chesapeake Bay rentals, or start a new search.


      There are no more results in Saint Michaels. Top of page