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.

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 127 reviews

CHESAPEAKE 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

$170 per night
Superhost

Apartment in Grasonville

4.89 out of 5 average rating, 173 reviews

Halcyon 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

$146 per night
Guest favorite

Houseboat in Grasonville

4.99 out of 5 average rating, 113 reviews

Cass-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

$150 per night

Popular amenities for Queen Anne's County vacation rentals

Other great vacation rentals in Queen Anne's County

Guest favorite

Home in Greensboro

4.95 out of 5 average rating, 44 reviews

Cozy 2 bedroom home on wooded private lane

Feb 5 – 12

$113 per night
Superhost

Guesthouse in Centreville

4.83 out of 5 average rating, 71 reviews

Centreville Cottage

Sep 2 – 9

$133 per night
Guest favorite

Farm stay in Centreville

4.96 out of 5 average rating, 51 reviews

3 bedroom home with pool and game room

Sep 30 – Oct 7

$209 per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 64 reviews

Waterfront historic district 1BR Apartment

Feb 3 – 10

$141 per night
Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

Aug 20 – 27

$125 per night
Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 95 reviews

Downtown Studio Apartment

Jan 4 – 11

$120 per night
Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 99 reviews

Red, White & Waterview Studio Apt with pool

Nov 26 – Dec 3

$119 per night
Guest favorite

Home in Grasonville

5.0 out of 5 average rating, 19 reviews

Bay Breeze-Chester River Retreat

Sep 26 – Oct 3

$397 per night
Guest favorite

Barn in Queenstown

5.0 out of 5 average rating, 40 reviews

Waterfront Modern Guest Barn

Aug 23 – 30

$540 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr 5 – 12

$450 per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 27 reviews

Eastern Neck Water Paradise w/Brick oven & Beach

Dec 20 – 27

$695 per night
Guest favorite

Guesthouse in Chester

5.0 out of 5 average rating, 39 reviews

Waterfront Guest Cottage: Sunsets, Pool, Pier

Jan 11 – 18

$599 per night

Destinations to explore