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Holiday Homes and Apartments Ridgely, MD and nearby

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All 31 Rentals in the Ridgely Area
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The following rentals are within 40 kilometres of Ridgely, Maryland.

From
$304
Per Night
1 / 15
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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From
$109
Per Night
1 / 31
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Trappe
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
From
$208
Per Night
1 / 28
Centreville
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (3) Make Enquiry
From
$304
Per Night
1 / 17
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s... View all property information
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From
$547
Per Night
1 / 13
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St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
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,... View all property information
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5 of 5 stars Reviewed 10 September 2014
The home was absolutely beautiful. Right around the corner from the town. Perfect location! We had been to St. Michaels 3 times before this trip and now we finally found our...
5 of 5 stars Reviewed 20 August 2014
Very comfortable, well furnished and equipped house with both modern and historical features. We took advantage of the great location to walk to tourist sites, restaurants and...
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From
$359
Per Night
1 / 12
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Chestertown
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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3 of 5 stars Reviewed 18 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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From
$456
Per Night
1 / 22
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St. Michaels
4 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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... View all property information
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From
$170
Per Night
1 / 11
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Chestertown
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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... View all property information
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5 of 5 stars Reviewed 30 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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From
$353
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 24 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
$182
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 21 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
$194
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
$146
Per Night
1 / 28
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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,... View all property information
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5 of 5 stars Reviewed 11 June 2014
My husband and I were lucky enough to stay in a charming little guest house on the Bay (Tolchester area of Chestertown, MD). House is almost right on the water, very clean, very...
5 of 5 stars Reviewed 10 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...
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From
$120
Per Night
1 / 10
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Safe
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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... View all property information
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5 of 5 stars Reviewed 13 November 2014
Would definitely stay again or recommend to friends. Off the beaten path but a stone's throw from everything. Clean, nicely furnished with an eye for the aesthetic. Simple and...
5 of 5 stars Reviewed 26 July 2014
We enjoyed our stay in this very pleasant and bright apartment, walking distance to the visitor's center, the downtown with many shops and restaurants, and the Chester River. The...
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From
$109
Per Night
1 / 33
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Greensboro
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
HOME ON THE RIVER: A view of Choptank River (read James Michener's 'Chesapeake') from all rooms in cozy 2 bedroom apartment with full kitchen & bath. Separate entrance, patio, dock with canoe and kayaks. Peaceful setting within 2 miles of town and relatively close to Washington D.C., Baltimore.&... View all property information
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From
$219
Per Night
1 / 12
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Rock Hall
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and... View all property information
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From
$699
Per Night
1 / 23
Centreville
4 Bedrooms, 4 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$254
Per Night
1 / 11
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Stevensville
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
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... View all property information
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From
$608
Per Night
1 / 29
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Trappe
8 Bedrooms, 6 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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... View all property information
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From
$304
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
  • 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
$1,823
Per Night
1 / 7
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Oxford
Studio, 4 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
  • Satellite TV
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
$315
Per Night
1 / 9
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Garden
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Camellia Cottage is a ca. 1950 ranch house apartment located on the property of the award-winning Brampton Bed & Breakfast Inn. The newest accommodation at our Chestertown Bed and Breakfast is a chic, Danish Modern furnished one bedroom flat. With it's own entrance, a fully equipped kitchen and a... View all property information
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From
$304
Per Night
1 / 12
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Easton
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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... View all property information
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From
$547
Per Night
1 / 12
Grasonville
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
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From
$923
Per Night
1 / 38
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St. Michaels
6 Bedrooms, 6 Bathrooms, Sleeps 12
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
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
$1,737
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
$340
Per Night
1 / 9
St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
$1,389
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
$6,382
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
$6,686
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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From
$868
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
$304
Per Night
1 / 29
Magnolia, DE
6 Bedrooms, 3 Bathrooms, Sleeps 17
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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
Enjoy a week at this OCEAN BLOCK 6 bedroom home sleeping 17 people. Just steps to the board walk and downtown, this home will serve as your base in S. Rehoboth where you can enjoy the public, guarded beach and all that downtown Rehoboth has to offer including a fantastic range of restaurants and... View all property information
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