Vacation rentals in Queen Anne's County

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Top-rated vacation rentals in Queen Anne's County

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Guest favorite

Apartment in Stevensville

4.97 out of 5 average rating, 239 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Oct 17 – 24

G$41,125 GYD 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.

Dec 12 – 19

G$34,925 GYD per night

Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 224 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

Nov 26 – Dec 3

G$116,662 GYD per night

Guest favorite

Guesthouse in Wye Mills

4.93 out of 5 average rating, 15 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

Dec 24 – 31

G$18,121 GYD per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 130 reviews

Chestertown - Eastern Shore Getaway

"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.

Sep 1 – 8

G$28,343 GYD per night

Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 102 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Jan 18 – 25

G$28,448 GYD per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Oct 1 – 8

G$29,265 GYD per night

Guest favorite

Home in Greensboro

4.96 out of 5 average rating, 46 reviews

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

Nov 5 – 12

G$26,818 GYD per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Sep 17 – 24

G$111,800 GYD per night

Guest favorite

Apartment in Chester

4.97 out of 5 average rating, 234 reviews

Cozy Waterfront Apartment Chester, MD

*We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to sit & enjoy beautiful water views!

Feb 3 – 10

G$25,842 GYD per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 205 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Sep 18 – 25

G$58,282 GYD per night

Guest favorite

Camper/RV in Chestertown

4.89 out of 5 average rating, 123 reviews

Cozy Airstream on a beautiful horse farm

You'll love this cozy 32' 1989 Airstream Excella 1000. It's got a comfy queen size bed in the bedroom and a couch that converts to a full size bed that could sleep another adult comfortably or a couple of kids. The farm is beautiful - you'll feel like you're on vacation. We have a fire pit out front and an 8' galvanized shallow trough pool in the summer. Complete with stove, fridge, microwave, gas grill and Keurig.

Jun 9 – 16

G$27,156 GYD per night