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House holiday rentals in Queen Anne's County

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Top-rated house rentals in Queen Anne's County

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Home in Chester

4.89 out of 5 average rating, 150 reviews

Kent Island Beautiful 4 BR home, central location!

Come enjoy all that Kent island has to offer--golfing, fishing, crabbing and the laid back island life! Beautifully remodeled 4 Bedroom house in a great community close to Rt 50, mins from the Bay Bridge!! Whether you are on Maryland's picturesque Eastern shore for its beaches & water activities or at the popular Kent Island wedding destinations for an event, this house is perfect for you!! Best value for large groups of up to 14! Plenty of comfy beds, a crib + gourmet kitchen and 2.5 baths!

Guest favourite

Home in Rock Hall

4.98 out of 5 average rating, 48 reviews

Eastern Neck Water Paradise w/Brick oven & Beach

This beautiful breathtaking waterfront home is the perfect place for your vacation. This spacious 3 story house sits along the back waters of the Chesapeake Bay, along Grey’s Inn Creek with it’s own private pier and beach area!! Kayaks and paddle boards available for guests to use! The water is 6’-9’ deep depending on the tide. You can bring your own boat or if you’re interested in renting one, Lankford Bay Marina is only 15 minutes by car or boat, must have a MD boaters safety card to rent

Guest favourite

Home in Rock Hall

5 out of 5 average rating, 22 reviews

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

Guest favourite

Home in Rock Hall

5 out of 5 average rating, 82 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Guest favourite

Home in Grasonville

4.95 out of 5 average rating, 258 reviews

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Guest favourite

Home in Stevensville

5 out of 5 average rating, 125 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

Guest favourite

Home in Stevensville

4.92 out of 5 average rating, 191 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room & kitchen! Perfect for Families & sleeps 11. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (11 max.). Book Today!

Home in Queenstown

4.81 out of 5 average rating, 155 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Guest favourite

Home in Chestertown

4.97 out of 5 average rating, 104 reviews

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Guest favourite

Home in Stevensville

5 out of 5 average rating, 105 reviews

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Guest favourite

Home in Denton

4.94 out of 5 average rating, 116 reviews

Mallard Landing Townhouse

Welcome to Maryland’s Eastern Shore and your own private townhouse in a quiet and peaceful neighborhood. You’ll be conveniently located less than an hour to the beaches, with short travel to Easton, Dover, D.C. and Baltimore. But why bother traveling when your in the beautiful historic town of Denton and all it has to offer with many up and coming stores, restaurants, and many other sights to enjoy including the Choptank River, Martinak State Park, Tuckahoe State Park, and historic downtown.

Guest favourite

Home in Chestertown

5 out of 5 average rating, 179 reviews

Totally Renovated historic house near town center

Renovated 19th century home. 3 king beds, 2 queens. 55” TV in family room, 2 more. 1st floor bedroom with full bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from Wash College and the C'town waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 more bedrooms with queens. 1 loft connected to a 2nd story bedroom with 2 twins. Fenced yard and an acre of private gardens. Fire pit. New Weber grill

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Popular amenities for Queen Anne's County house rentals

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Air conditioning

House rentals with a pool

Guest favourite

Home in Rock Hall

4.94 out of 5 average rating, 35 reviews

Rockfish Keeper

Guest favourite

Home in Denton

4.95 out of 5 average rating, 22 reviews

*NEW* The Wilder Way

Guest favourite

Home in Chester

4.99 out of 5 average rating, 81 reviews

Waterfront Farmhouse Meets Modern Luxury

Guest favourite

Home in Church Hill

4.89 out of 5 average rating, 53 reviews

Private Peaceful Waterfront House w/ Pool, Hot Tub

Guest favourite

Home in Stevensville

5 out of 5 average rating, 29 reviews

Wildbluesea Retreat

Guest favourite

Home in Stevensville

5 out of 5 average rating, 15 reviews

Bayside Escape

Guest favourite

Home in Millington

4.89 out of 5 average rating, 54 reviews

The Peaceful Getaway (with private pool & hot tub)

Weekly house rentals

Guest favourite

Home in Rock Hall

5 out of 5 average rating, 12 reviews

Bay Beach Oasis

Home in Chestertown

4.76 out of 5 average rating, 17 reviews

Langford Creek | Waterfront w/ HOT TUB + Fire Pit!

Guest favourite

Home in Stevensville

4.91 out of 5 average rating, 77 reviews

Cheerful & Spacious Shore Life Beauty!

Guest favourite

Home in Stevensville

5 out of 5 average rating, 6 reviews

Sleeps12*MainHouse+DetachedApt*Wedding Venues&USNA

Guest favourite

Home in Chestertown

5 out of 5 average rating, 34 reviews

Magnolia House: walk to shops, restaurants, river

Guest favourite

Home in Chester

5 out of 5 average rating, 33 reviews

*Waterfront Sunset Bayview* sleeps 6

Guest favourite

Home in Chestertown

5 out of 5 average rating, 33 reviews

In Town Chestertown Rancher (1 Block to College)

Guest favourite

Home in Annapolis

4.98 out of 5 average rating, 94 reviews

Hot Tub Haven: Backyard Oasis & Winter Discounts

Private house rentals

Guest favourite

Home in Chestertown

4.97 out of 5 average rating, 29 reviews

River Cottage, Chestertown

Guest favourite

Home in Grasonville

5 out of 5 average rating, 44 reviews

Bay Breeze-Chester River Retreat

Guest favourite

Home in Rock Hall

5 out of 5 average rating, 29 reviews

1-Particular Harbor: A Coastal Oasis!

Guest favourite

Home in Denton

4.9 out of 5 average rating, 87 reviews

Historic 19th Century Eastern Shore Farmhouse

Home in Chester

4.83 out of 5 average rating, 6 reviews

Crab Alley Bay House, Waterfront Home w Hot Tub

Guest favourite

Home in Annapolis

4.9 out of 5 average rating, 198 reviews

Country House on the Bay

Guest favourite

Home in Chester

5 out of 5 average rating, 66 reviews

Chester Delight- Fireplace/Deck&Patio+fenced yard

Guest favourite

Home in Annapolis

5 out of 5 average rating, 25 reviews

Bay Home in Annapolis with Private Dock

Destinations to explore