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Holiday villas in Chesapeake Beach, MD

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All 27 Rentals in the Chesapeake Beach Area
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The following rentals are within 30 kilometers of Chesapeake Beach, Maryland.

From
€202
Per Night
1 / 6
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Tilghman
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (1) Make Enquiry
From
€363
Per Night
1 / 13
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St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Details Reviews (5) Make Enquiry
From
€303
Per Night
1 / 22
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St. Michaels
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (1) Make Enquiry
From
€141
Per Night
1 / 20
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Tilghman
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
€202
Per Night
1 / 8
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Davidsonville
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Pool
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
2 bedroom, 2 bath with living salon, kitchen, and an aft deck View all property information
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From
€210
Per Night
1 / 10
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Saint Leonard
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Garden
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and... View all property information
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From
€202
Per Night
1 / 14
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Oxford
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Housekeeping...
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautifully renovated home sleeps 6. Full master suite with sitting area, steam shower & soaking tub. Second bedroom has full-sized bed. Queen sized murphy bed in den. Chef's kitchen with five burner stove & side warming oven and four-person breakfast counter. Wood-burning stove in living room,... View all property information
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From
€161
Per Night
1 / 9
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North Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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... View all property information
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From
€1,211
Per Night
1 / 7
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Oxford
Studio, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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. View all property information
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From
€613
Per Night
1 / 38
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St. Michaels
6 Bedrooms, 6 Bathrooms, Sleeps 12
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Garden
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
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From
€202
Per Night
1 / 11
Claiborne
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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5 of 5 stars Reviewed 11 October 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...
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From
€109
Per Night
1 / 17
North Beach
1 Bedroom, 1 Bathroom, Sleeps 5
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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5 of 5 stars Reviewed 15 November 2014
Just as described- walk to boardwalk and shops. Owner right next door, he's thought of everything. Lovely getaway destination.
5 of 5 stars Reviewed 8 July 2013
We absolutely fell in love with this quiet little cabin a block away from Chesapeake Bay. Gary, the owner, met us at the cabin and personally gave us a tour of the cabin and let...
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From
€283
Per Night
1 / 12
Tilghman
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Garden
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Black Walnut Point Inn – A Secret Place of Peace. Just 20 minutes past St. Michaels on 58-acres of bird sanctuary, Black Walnut Point offers peace and quiet with unobstructed water views in every direction. The private estate was once sealed off by Russian spies and the First Gulf War was planned... View all property information
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5 of 5 stars Reviewed 26 August 2012
After a very rocky and delayed start to our anniversary trip we arrived at 5am to Black Walnut Point Inn. I stayed awake to watch the sunrise and it was worth it. So peaceful and...
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From
€153
Per Night
1 / 7
St. Michaels
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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5 of 5 stars Reviewed 19 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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From
€303
Per Night
1 / 9
Bozman
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
€121
Per Night
1 / 20
St. Michaels
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
The historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from all museums, parks, restaurants, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two individuals in Talbot County... View all property information
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5 of 5 stars Reviewed 22 August 2014
The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
5 of 5 stars Reviewed 20 July 2014
We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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From
€291
Per Night
1 / 12
St. Michaels
7 Bedrooms, 3 Bathrooms, Sleeps 11
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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5 of 5 stars Reviewed 27 September 2014
Friends and family stayed at the home to watch my nephew get married on 9/20/14. I must say, the house was as much of the event as the wedding celebration. We went from 6 of us...
5 of 5 stars Reviewed 23 July 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...
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From
€537
Per Night
1 / 7
Bozman
4 Bedrooms, 2 Bathrooms, Sleeps 13
Details Reviews (8) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
€242
Per Night
1 / 17
Riva
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
You'll love the stunning 180-degree view of the South River, just off the Chesapeake Bay near Annapolis. The location is incredible. Just six miles from Annapolis and the United States Naval Academy. The home is 15 miles from Baltimore/Washington International Airport and 40 minutes to Washington,... View all property information
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From
€923
Per Night
1 / 16
St. Michaels
6 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations Inc on the Eastern Shore presents another luxurious waterfront home. Only minutes from the famous historic “Chestertown”, this magnificent 1000 acre estate is both a wildlife sanctuary and arboretum, with hundreds of mature specimen trees and acres of woods and farm fields. The... View all property information
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From
€282
Per Night
1 / 17
North Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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),... View all property information
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From
€226
Per Night
1 / 9
St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
€202
Per Night
1 / 12
Deale
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
€1,154
Per Night
1 / 16
St. Michaels
6 Bedrooms, 7 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations Inc on the Eastern Shore presents another luxurious waterfront vacation home. This is where your dreams come true! Your vacation begins with a drive down a country lane surrounded by farmland or perhaps even arriving on your own helicopter. You have entered another world – one... View all property information
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From
€576
Per Night
1 / 11
St. Michaels
5 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations in St Michaels is excited to present the Virginia (also known as Duxbury Point Manor as one of our more popular vacation homes on the water near St Michaels This enchanting Manor home overlooking the broad waters of Leadenham Bay, has a pool, a dock and a floating 18ft dock... View all property information
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From
€4,239
Per Week
1 / 16
St. Michaels
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Another luxury vacation rental home by Tidewater Vacations Inc on the Eastern Shore. This gorgeous, traditional country home is nestled amongst trees on magnificent grounds overlooking the Wye River.The secluded estate is ideally located close to the historic towns of Easton and St Michaels and... View all property information
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From
€4,441
Per Week
1 / 16
St. Michaels
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tidewater Vacations of St Michaels presents a historic, charming vacation rental just minutes from Easton and St Michaels. Savanna is truly one of Maryland’s oldest and most picturesque vacation rental homes on the Miles River in Talbot County. Dating from 1659 and throughout the years, Savanna... View all property information
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