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Best Vacation rentals and Airbnb offers in Queenstown, MD
10 60 reviews
Queenstown, MD
09/02 – 09/11
$737/nighttotal: $6633 (9 )
Gorgeous Creek Side Ranch-style Estate With Dock
4 5
apartment , Grasonville
This Chesapeake Bay waterfront farmhouse rental in Queenstown, Maryland's Eastern Shore, offers a private dock on Sadler's Cove, a short drive from Eastern Shore attractions. The 4-bedroom, 2-bathroom home sleeps 11 guests and features a fully equipped kitchen, high-speed internet (500 Mbps), smart TVs, a firepit, propane grill, and access to a fenced backyard; abundant wildlife viewing is also available.
Queenstown, MD
09/02 – 09/11
$992/nighttotal: $8928 (9 )
Wye Topia
1 5
house , Queenstown
This Grasonville, Maryland home, near Annapolis Harbor (26 miles) and Sandy Point State Park (18 miles), offers easy access to historical sites like the US Naval Academy and the Maryland State House. This 3,660-square-foot house boasts four bedrooms, four bathrooms, a private pool, free Wi-Fi, parking, and a fully equipped kitchen, comfortably accommodating up to 21 guests.
Queenstown, MD
09/02 – 09/11
$932/nighttotal: $8388 (9 )
Centreville Waterfront Farm - 170 Acres - Pool - Private Dock - Private Beach
1 5
house , Queenstown
This waterfront home near Centreville, Maryland, offers luxurious accommodations 42 miles from Baltimore/Washington International Thurgood Marshall Airport. The 2,800-square-foot house features four bedrooms, five bathrooms, a private dock and beach, a swimming pool, free Wi-Fi, parking, and sleeps up to 19 guests.
10 7 reviews
Queenstown, MD
09/02 – 09/11
$344/nighttotal: $3096 (9 )
| Eastern Shore | Family Getaway
1 5
apartment , Centreville
This apartment is located on Maryland's Eastern Shore, just a short drive from the Wye River and the charming historic towns of Centreville, Chestertown, Easton, and Saint Michael's. It boasts excellent ratings for location, cleanliness, and overall user experience. The home features four bedrooms and two bathrooms, comfortably accommodating up to ten guests. This rental offers a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, parking, internet access, and a variety of outdoor activities like cornhole, spike ball, and frisbee.
9.2 12 reviews
Queenstown, MD
09/02 – 09/11
$412/nighttotal: $3708 (9 )
Peaceful Queenstown Home W/ Deck & Grill!
4 5
apartment , Queenstown
This five-bedroom Queenstown vacation home is located 2.2 miles from Wye Oak State Park and under 6 miles from Queenstown Premium Outlets and Queenstown Harbor Golf Links. This 2,340-square-foot property boasts three bathrooms, sleeps eight guests, and includes a fitness center, spa, and fully equipped kitchen with modern appliances.
9.6 33 reviews
Queenstown, MD
09/02 – 09/11
$395/nighttotal: $3555 (9 )
Peaceful Queenstown Home W/ Deck & Grill!
4 5
apartment , Queenstown
This Queenstown, Maryland vacation rental is located in a family-friendly neighborhood, offering easy access to Terrapin Nature Park. This spacious four-bedroom, 2.5-bathroom house comfortably sleeps eight guests and features a fully equipped kitchen, a large deck, a gas grill, a fire pit, a home gym, smart TVs, an electric fireplace, keyless entry, free WiFi, and garage parking for up to ten vehicles, including an EV charger.
10 2 reviews
Queenstown, MD
09/02 – 09/11
$1030/nighttotal: $9270 (9 )
Wye Topia | An Esvr Property
4 5
apartment , Queenstown
This Wye River waterfront home, located in a rural area outside Queenstown, offers scenic views and is a short drive from Queenstown's attractions, though precise distances aren't specified. This 3,600-square-foot vacation rental boasts four bedrooms, three bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, swimming pool, and a spacious open-floor plan.
9.9 93 reviews
Queenstown, MD
09/02 – 09/11
$477/nighttotal: $4293 (9 )
Get Away To The Beautiful Wye River
1 5
apartment , Grasonville
This Grasonville vacation home, situated on Maryland's Eastern Shore near the Wye River, offers easy access to Queenstown Harbor golf course, Pintail Point sporting clays, and Queenstown Outlets. Sleeping up to 11 guests in a house with two bathrooms, this rental boasts a private dock on the Wye River, a garden, tennis court, and amenities including a fridge, microwave, dishwasher, and air conditioning; nearby attractions include the Wye Island Natural Resource Management Area.
10 20 reviews
Queenstown, MD
09/02 – 09/11
$307/nighttotal: $2763 (9 )
Island Life 2! 2024 Remodeled Home On Private Waterfront Kent Island Estate
3 5
farm , Stevensville
This Stevensville, Maryland waterfront farm stay boasts 22 acres with pier access for crabbing and boating, situated 4.7 miles from Kent Island's restaurants and wedding venues, and a short drive from Annapolis. The three-bedroom, two-bathroom property sleeps eight guests and features a fully equipped kitchen with modern appliances, Wi-Fi, air conditioning, and Smart TVs, plus a private 1/4-mile driveway ideal for children's play.
10 66 reviews
Queenstown, MD
09/02 – 09/11
$615/nighttotal: $5535 (9 )
*Newhottub*luxurycoastal*closetoweddingvenues
4 5
apartment , Grasonville
This Grasonville home, located on Kent Island, is within one mile of restaurants, marinas, live music venues, and numerous wedding venues. The 4-bedroom, 3-bathroom house sleeps up to 12 guests and boasts a fully equipped kitchen, a jacuzzi, and a large deck overlooking the Chesapeake Bay, perfect for enjoying stunning sunsets.
9.8 95 reviews
Queenstown, MD
09/02 – 09/11
$370/nighttotal: $3330 (9 )
Serene Waterfront Cottage With Dock And Gorgeous Views.
1 5
apartment , Rock Hall
This waterfront vacation home is located in Rock Hall, just minutes from The Mainstay, Rock Hall Harbor, and Waterman’s Museum, offering easy access to the area's best attractions. Guests consistently rate the location, cleanliness, and overall experience as excellent. The rental features one bedroom and can accommodate up to seven guests. Enjoy modern comforts including air conditioning, a fully equipped kitchen, a private garden, and a spacious terrace with stunning views of the Chesapeake Bay.
9.5 4 reviews
Queenstown, MD
09/02 – 09/11
$681/nighttotal: $6129 (9 )
Kent Island Comfort 4br Home Minutes From Waterfront, Wineries & Nature Trails
3 5
house , Chester
This Chester, Maryland house rental, minutes from Kent Island's waterfront, wineries, and nature trails, offers convenient access to local attractions. The 10,760-square-foot home boasts three bedrooms, three bathrooms, sleeps seventeen guests, and includes amenities such as a fully equipped kitchen, free Wi-Fi, private parking, and a billiards table.
Choose the Right Family-Friendly Vacation Rentals in Queenstown, MD
These family-friendly vacation rentals in Queenstown, MD offer spacious layouts and easy access to top city attractions.
9.1 1605 reviews
Queenstown, MD
09/02 – 09/11
$466/nighttotal: $4194 (9 )
Holiday Inn Express Annapolis East-kent Island By Ihg
2 5
resort , Kent Narrows
The Holiday Inn Express Annapolis East-Kent Island is located in Grasonville, just a short drive from the charming town of Kent Narrows and its waterfront restaurants, as well as the historical attractions of Annapolis Harbor. This hotel has received very good user ratings, excellent location ratings, and very good cleanliness ratings. The hotel has 270 square foot rooms with one bedroom and one bathroom. Guests can enjoy amenities such as a swimming pool, tennis court, fitness center, restaurant, bar, and free parking.
8.0 1 review
Queenstown, MD
09/02 – 09/11
$1028/nighttotal: $9252 (9 )
Queenstown Waterfront | Boat Ramp | Pool | Private Dock
4 5
apartment , Queenstown
This luxurious Queenstown waterfront home sits within three miles of the Queenstown Premium Outlets and Queenstown Harbor Golf Links, and six miles from the Queenstown Harbor Golf Club and Wye Oak State Park. This 3,660-square-foot residence boasts four bedrooms, four bathrooms, sleeps eleven guests, and features a private pool, tennis court, and game room.
10 44 reviews
Queenstown, MD
09/02 – 09/11
$989/nighttotal: $8901 (9 )
Sunset Lodge On The Bay
6 5
apartment , Rock Hall
This 5,000-square-foot waterfront home in Rock Hall, Maryland, sits on a 58-acre private estate, three miles from Rock Hall's Main Street and near Eastern Neck National Wildlife Refuge. This six-bedroom, four-bathroom house sleeps fourteen guests and boasts a game room, bar, private beach access, and stunning Chesapeake Bay views, along with amenities including a dishwasher, air conditioning, and ample parking.
10 10 reviews
Queenstown, MD
09/02 – 09/11
$663/nighttotal: $5967 (9 )
Kent Island Luxury Waterfront
4 5
apartment , Stevensville
This Stevensville waterfront home offers stunning views and easy access to Love Point State Park, located within 6 miles of Paul Reed Smith Guitars and under 9 miles from Matapeake State Park and the Chesapeake Exploration Center. This four-bedroom, four-bathroom vacation rental sleeps 14 guests and boasts a fully equipped kitchen, private balcony, garden, spa, and free WiFi; enjoy outdoor grilling and a cozy fireplace.
Best Queenstown, MD vacation rentals with parking
10 2 reviews
Queenstown, MD
09/02 – 09/11
$1470/nighttotal: $13230 (9 )
Blake House Historic Estate With Private Inn
6 5
house , Centreville
Blake House Historic Estate, a spacious 6-bedroom villa in Centreville, Maryland, is located 21 miles from the Academy of the Arts and 24 miles from Sandy Point State Park. This 5,010-square-foot property boasts a private pool, fitness center, fully equipped kitchen, and accommodates up to 20 guests, offering convenient amenities like free Wi-Fi and on-site parking.
Queenstown, MD
09/02 – 09/11
$1104/nighttotal: $9936 (9 )
A Stunning Chesapeake Bay Sunset From A Beautiful Home With An Inground Pool!!
6 5
apartment , Rock Hall
This waterfront home in Rock Hall offers direct Chesapeake Bay views, situated near the Historical Society of Kent County Maryland and Eastern Neck National Wildlife Refuge. This 6-bedroom, 2-bathroom house accommodates up to 10 guests and features a full kitchen, air conditioning, a swimming pool, garden, and parking.
9.0 2 reviews
Queenstown, MD
09/02 – 09/11
$300/nighttotal: $2700 (9 )
River Cottage, Chestertown
2 5
apartment , Edesville
This Edesville cottage, near the Chester River and 15 minutes from Washington College, offers a peaceful riverside location with easy access to Chestertown attractions. The 1180-square-foot home features two bedrooms, one bathroom, a loft with bunk beds, accommodating up to six guests, and includes amenities such as kayaks, bikes, a fire pit, and a private backyard.
10 1 review
Queenstown, MD
09/02 – 09/11
$871/nighttotal: $7839 (9 )
Crab Alley | Waterfront Home + Hot Tub + Game Room
4 5
apartment , Chester
This Bayfront residence in Chester, Maryland, offers direct water access and is located within 3 miles of Queenstown Premium Outlets and Matapeake State Park. This 4-bedroom, 2-bathroom house accommodates up to 8 guests and features a private hot tub, a boat dock, a game room with a pool table, and an expansive kitchen.
Frequently Asked Questions about vacation rentals in Queenstown, MD
Which walking or cycling routes are the best in Queenstown, MD?
The Queenstown Heritage Trail is a nice, easy walk through town, and the scenic bike route along the Choptank River is popular with cyclists. If you're looking for a longer ride, you can bike to St. Michaels, about 10 miles away.
What are the best Airbnb and vacation rentals in Queenstown, MD?
What other towns or cities can be easily accessed from Queenstown, MD?
Queenstown is a great base for exploring the Eastern Shore. You can easily drive to St. Michaels, Easton, Cambridge, and even Annapolis in about an hour or two.
What are the most popular Airbnbs in Queenstown, MD?
What amenities are commonly available in vacation rentals in Queenstown, MD?
Most vacation rentals in Queenstown have basic amenities like a kitchen, bathroom, and bedrooms. Many also offer extras like a washer and dryer, a fireplace, and a deck or patio. Some even have private pools or hot tubs.
What are the best vacation rentals with a pool in Queenstown, MD?
What time of year is best to rent a vacation rental Queenstown, MD?
The best time to visit Queenstown is in the spring or fall when the weather is mild and the crowds are smaller. The summer can be hot and humid, but it's a great time to enjoy the beach and outdoor activities. The winter is quiet, but it can be cold and wet.
What are the best rentals for families and kids in Queenstown, MD?
Guest-Favorite Vacation Rentals with a Terrace in Queenstown, MD
Start your morning right with a vacation rental in Queenstown, MD featuring a private balcony and stunning views.
10 79 reviews
Queenstown, MD
09/02 – 09/11
$1636/nighttotal: $14724 (9 )
Blake House Historic Estate With Private Inn
6 5
house , Centreville
This Centreville, Maryland estate, a 1691 colonial home combined with the relocated 1735 Crown and Anchor Inn, sits on 12 acres with direct water access, its precise location within Centreville requiring further specification for proximity to landmarks. The 5,010-square-foot property features six bedrooms, six bathrooms, and accommodates up to 12 guests, offering amenities such as a swimming pool, fitness center, and extensive outdoor recreational facilities including bocce ball courts, a sauna, and nature trails, plus indoor entertainment in the Crown and Anchor Inn.
8.8 11 reviews
Queenstown, MD
09/02 – 09/11
$276/nighttotal: $2484 (9 )
Kent Island Waterfront Cottage
2 5
apartment , Stevensville
This waterfront cottage in Stevensville offers direct access to the Chester River, featuring a 250-foot pier with underwater lights and proximity to Love Point State Park and Queenstown Harbor Golf. This 2-bedroom, 1-bathroom rental accommodates up to 6 guests and includes a kitchen with a fridge and microwave, air conditioning, a terrace, garden, spa, and parking, with family-friendly amenities available upon request.
10 17 reviews
Queenstown, MD
09/02 – 09/11
$537/nighttotal: $4833 (9 )
Island Blue Getaway! Brand New Charming Family Friendly Home On Kent Island Md
3 5
apartment , Chester
This Kent Island vacation home in Chester, Maryland, offers easy access to the Chesapeake Bay Bridge and Annapolis, placing you minutes from attractions like the Hammond-Harwood House and Sandy Point State Park. This 2200-square-foot property boasts three bedrooms, three bathrooms, and sleeps eight, featuring a fully equipped kitchen with dishwasher, air conditioning, a terrace, and parking; enjoy water views of Cox Creek, plus nearby opportunities for boating, fishing, hunting, and cycling.
9.8 4 reviews
Queenstown, MD
09/02 – 09/11
$430/nighttotal: $3870 (9 )
Peaceful Queenstown Home W/ Deck & Grill!
4 5
house , Queenstown
This Grasonville vacation home, located 16 miles from the Academy of the Arts and 20 miles from Sandy Point State Park, offers a peaceful retreat near Annapolis attractions (27-29 miles). The 2,340-square-foot property features a spacious four-bedroom layout accommodating up to 15 guests, complete with a fully equipped kitchen, spa, fitness center, and ample parking.
Top-Rated Pet-Friendly Vacation Rentals in Queenstown, MD
Stay in a pet-friendly vacation rental in Queenstown, MD situated near dog parks and city walks, ensuring a comfortable stay for both you and your pet.
8.2 20 reviews
Queenstown, MD
09/02 – 09/11
$525/nighttotal: $4725 (9 )
Inn At Haven Harbour
1 5
resort , Rock Hall
The Inn at Haven Harbour is a short drive from Rock Hall's waterfront and marinas, offering easy access to the town's charm and activities. The resort consistently receives excellent ratings for location, cleanliness, and overall experience. The Inn at Haven Harbour features a private beach area with direct access to the Chesapeake Bay, perfect for swimming and water sports. Guests can enjoy amenities like a seasonal outdoor pool, fitness center, and complimentary bikes, as well as on-site dining and a shared lounge and bar.
10 2 reviews
Queenstown, MD
09/02 – 09/11
$1805/nighttotal: $16245 (9 )
Private Boat Dock! Wye River Retreat In Queenstown
5 5
apartment , Grasonville
This Grasonville waterfront vessel offers private access and is conveniently located near the Pickering Creek Audubon Center and the Chesapeake Bay Maritime Museum. The 4,500-square-foot houseboat boasts five bedrooms, five bathrooms, a private pool, and can comfortably accommodate up to ten guests, with amenities including a full kitchen, laundry facilities, and Wi-Fi.
10 5 reviews
Queenstown, MD
09/02 – 09/11
$338/nighttotal: $3042 (9 )
Comfortable Single Floor Living
1 5
apartment , Grasonville
This Grasonville apartment offers a 3-acre country setting, a short drive from local attractions and waterfronts. This 3-bedroom, 2-bathroom residence accommodates up to 8 guests with a split bedroom design, indoor bar, covered deck, sport court, and fenced outdoor space, featuring accessible entry and versatile sleeping arrangements.
9.9 27 reviews
Queenstown, MD
09/02 – 09/11
$324/nighttotal: $2916 (9 )
â«· Massey On The Lake
1 5
apartment , Queenstown
This 5-bedroom home is located on a private 1-acre property on Wye Lake, offering direct access for fishing and kayaking. It has excellent user, location, and cleanliness ratings. This charming farmhouse offers a unique rustic experience with remnants of its past as a working farm. It comfortably accommodates up to 10 guests and features a corn hole game, volleyball court, lake trail, gas grill, picnic table, and access to a nearby pool.