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Vacation rentals in Chester, MD and nearby

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    All 41 Rentals in the Chester Area
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    From
    $225
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    1 / 21
    5 of 5 stars (2) Excellent
    Chester
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    $469
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    1 / 37
    Chester
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    The following rentals are within 25 kilometres of Chester, Kent Island, Maryland.

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    $313
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    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    $313
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    1 / 17
    5 of 5 stars (3) Excellent
    Rock Hall, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview 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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    1 / 31
    5 of 5 stars (1) Excellent
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    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.... View all property information
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    $532
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    1 / 30
    4.5 of 5 stars (2) Very good
    Annapolis, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travellers have booked this property
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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
    • x
    • ?
    About this property
    Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking... View all property information
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    $938
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    1 / 26
    5 of 5 stars (2) Excellent
    Annapolis, MD
    6 Bedrooms / 5 Bathrooms / Sleeps 13
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms... View all property information
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    5 of 5 stars Reviewed 27 September 2014
    Our large group of women in their 30's had a great time and everyone had a comfortable bed and plenty of room. Caitlyn was very responsive, friendly and accommodating from the...
    5 of 5 stars Reviewed 11 August 2014
    We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large...
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    1 / 23
    5 of 5 stars (1) Excellent
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture, world-class restaurants & a vibrant, walkable capital city! Here in Upper Eastport, on a cul de sac, we are a short walk to the Historic Harbor & 3 blocks... View all property information
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    5 of 5 stars Reviewed 15 July 2014
    If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to...
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    1 / 13
    5 of 5 stars (5) Excellent
    St. Michaels, MD
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview 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 9 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 19 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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    $211
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    1 / 4
    5 of 5 stars (2) Excellent
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has twin beds. Large loft has queen size bed. Although the condo can accommodate 6 for sleeping, I will rent only to parties of 4 or fewer. Dining room can seat 8 + Washer and Dryer,... View all property information
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    5 of 5 stars Reviewed 29 June 2014
    We really enjoyed our stay at your condo. It was roomy and felt like home. It is in a very nice condo community which was very quiet. It was nice being able to cook and see into...
    5 of 5 stars Reviewed 12 November 2013
    My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a...
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    $469
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    1 / 22
    5 of 5 stars (1) Excellent
    St. Michaels, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    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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    $261
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    1 / 11
    Stevensville
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    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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    $438
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    1 / 25
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around... View all property information
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    $1,876
    / Night
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    1 / 15
    Annapolis, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation and building addition with exposed structure and mechanical systems that serves as the architect - owner's live-work getaway. The main house has a 4 stop elevator, 2 car garage, master bdrm and bath suite, 3 additional... View all property information
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    $250
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    1 / 18
    Annapolis, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview 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
    The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny or Midshipman at the Naval Academy. This house is modestly priced yet has all the amenities and comfort of a home and the ability to eat in and cook your meals in our huge fully equipped kitchen or barbecue... View all property information
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    $500
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    1 / 7
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please... View all property information
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    $438
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    1 / 21
    Arnold, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Clean, comfortable, family-friendly split-level home, fully furnished, washer and dryer, TV, cable, internet, wifi, quiet neighborhood with off-street parking, large shaded fenced back yard with deck for relaxing after a fun-filled day exploring Historic Annapolis, the Baltimore Harbor or our... View all property information
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    $369
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    1 / 6
    Annapolis, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Our home is located in the Eastport section of Annapolis and just a short walk to Main street, the Historic District and the Naval Academy. We have a large back yard that's great for entertaining, plenty of off street parking and we're just across the street from the best view of the Chesapeake Bay... View all property information
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    $875
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    1 / 6
    Annapolis, MD
    5 Bedrooms / 6 Bathrooms / Sleeps 12
    traveller have booked this property
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    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
    About this property
    Our home is brand new & only one block from the Naval Academy Stadium on Gibson Rd (you can see the stadium from M. bedroom balcony). With, 4 bedrooms upstairs & 1 bedroom down, all the bedrooms have their own full bath. There is also a family room on the second floor with a mini bar, sink & pull... View all property information
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    $225
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    1 / 12
    Rock Hall, MD
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    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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    $563
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    1 / 18
    St. Michaels, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    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... View all property information
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    $949
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    1 / 38
    St. Michaels, MD
    6 Bedrooms / 6 Bathrooms / Sleeps 12
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    • 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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    $744
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    1 / 26
    Annapolis, MD
    5 Bedrooms / 3 Bathrooms / Sleeps 20
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    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... View all property information
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    $375
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    1 / 9
    Annapolis, MD
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as... View all property information
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    $438
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    1 / 25
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around... View all property information
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    $625
    / Night
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    1 / 11
    Annapolis, MD
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This is the newly renovated 3-story open plan live-work unit that is connected to the main house that is similarly titled as the main house (1) and the studio apartment (2) - not included with this listing. Striking and dramatic 1500 - 1600 sf contemporary, open plan loft style renovation with a... View all property information
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    $238
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    1 / 13
    5 of 5 stars (1) Excellent
    St. Michaels, MD
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview 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 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.... View all property information
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    5 of 5 stars Reviewed 18 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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    $438
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    1 / 23
    5 of 5 stars (2) Excellent
    St. Michaels, MD
    7 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview 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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    $469
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    1 / 9
    5 of 5 stars (1) Excellent
    Bozman, MD
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    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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    $225
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    1 / 20
    5 of 5 stars (12) Excellent
    St. Michaels, MD
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview 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 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,... 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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    5 of 5 stars (1) Excellent
    Claiborne, MD
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    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 10 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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    5 of 5 stars (8) Excellent
    Bozman, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 13
    Overview 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
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    • Wheelchair access
    • Elder access
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    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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    $375
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    4.5 of 5 stars (3) Very good
    Centreville, MD
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    This house is on the former estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the Chester River and Chesapeake... View all property information
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    $625
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    1 / 13
    Annapolis, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac... View all property information
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    1 / 23
    Annapolis, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA. Private wooded setting with wonderful water views. 3 miles to Annapolis Historic district. Easy commute to Washington, DC and Baltimore, MD. Tastefully furnished and equipped. View all property information
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    1 / 23
    Stevensville
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    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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    1 / 12
    Grasonville, MD
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    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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    1 / 9
    St. Michaels, MD
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview 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
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    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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    $1,063
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    1 / 24
    Annapolis, MD
    4 Bedrooms / 4 Bathrooms / Sleeps 14
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek. Decks span the entire house 65' above the water. There are 4 full baths and 4 bedrooms... View all property information
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    $294
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    1 / 6
    Rock Hall, MD
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • Air Conditioning
    • Dryer
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    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending... View all property information
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    $438
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    1 / 22
    Annapolis, MD
    3 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of... View all property information
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