Vacation rentals in Queen Anne's County
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Top-rated vacation rentals in Queen Anne's County
Guests agree: these stays are highly rated for location, cleanliness, and more.
Home in Chestertown
4.94 out of 5 average rating, 127 reviewsCHESAPEAKE SUNSETS
Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.
Aug 6 – 13
Apartment in Grasonville
4.89 out of 5 average rating, 173 reviewsHalcyon house. Lovely views on MD eastern shore.
This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to some restaurants.
Feb 7 – 14
Houseboat in Grasonville
4.99 out of 5 average rating, 113 reviewsCass-Away A Luxury Houseboat
Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!
Feb 2 – 9
Vacation rentals for every style
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Popular amenities for Queen Anne's County vacation rentals
Other great vacation rentals in Queen Anne's County
Home in Greensboro
4.95 out of 5 average rating, 44 reviewsCozy 2 bedroom home on wooded private lane
Feb 5 – 12
Guesthouse in Centreville
4.83 out of 5 average rating, 71 reviewsCentreville Cottage
Sep 2 – 9
Farm stay in Centreville
4.96 out of 5 average rating, 51 reviews3 bedroom home with pool and game room
Sep 30 – Oct 7
Apartment in Chestertown
5.0 out of 5 average rating, 64 reviewsWaterfront historic district 1BR Apartment
Feb 3 – 10
Apartment in Rock Hall
4.96 out of 5 average rating, 47 reviewsBayside bungalow cottage by the sea
Aug 20 – 27
Apartment in Chestertown
4.92 out of 5 average rating, 95 reviewsDowntown Studio Apartment
Jan 4 – 11
Casa particular in Chestertown
4.93 out of 5 average rating, 99 reviewsRed, White & Waterview Studio Apt with pool
Nov 26 – Dec 3
Home in Grasonville
5.0 out of 5 average rating, 19 reviewsBay Breeze-Chester River Retreat
Sep 26 – Oct 3
Barn in Queenstown
5.0 out of 5 average rating, 40 reviewsWaterfront Modern Guest Barn
Aug 23 – 30
Home in Chestertown
5.0 out of 5 average rating, 75 reviewsRiver front cottage with private dock & water fun
Apr 5 – 12
Home in Rock Hall
5.0 out of 5 average rating, 27 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Dec 20 – 27
Guesthouse in Chester
5.0 out of 5 average rating, 39 reviewsWaterfront Guest Cottage: Sunsets, Pool, Pier
Jan 11 – 18
Destinations to explore
- Waterfront rentals Queen Anne's County
- Rentals with a fire pit Queen Anne's County
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- Rentals with a washer and dryer Queen Anne's County
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- Kid-friendly rentals Queen Anne's County
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- House rentals Queen Anne's County
- Rentals with a fireplace Queen Anne's County
- Rentals with pools Queen Anne's County
- Monthly Rentals Queen Anne's County
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