Vacation Rentals in Queenstown, MD

This waterfront property is conveniently located just 14.5 kilometres from Earle Landing, Hazel Miner Monument, and Queenstown Premium Outlets, offering easy access to local attractions and shopping. The house has consistently received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The spacious four-bedroom house spans 260 square metres and comfortably accommodates up to 10 guests. This family-friendly home features a private pool, a fireplace, a fully equipped kitchen, free Wi-Fi, BBQ grills, a garden, and a tennis court, providing ample opportunities for relaxation and entertainment.

This Queenstown property, situated in Grasonville, Maryland, is conveniently located approximately 42km from Annapolis Harbour and 29km from Sandy Point State Park.
This spacious 340 square metre house boasts four bedrooms, four bathrooms, a private swimming pool, free Wi-Fi, parking, and a fully equipped kitchen, comfortably accommodating up to 21 guests.

This charming apartment is situated in Wye Mills, a historic district on the shores of Wye Lake, just 5 kilometres from a swimming pool. The property has received excellent ratings for its cleanliness, location, and overall experience.
The apartment offers five bedrooms, two bathrooms, and can comfortably accommodate up to ten guests. Amenities include a fully equipped kitchen, a private garden, a gas grill, a picnic table, and a range of outdoor activities such as corn hole, volleyball, and a nature trail.

The Holiday Inn Express Annapolis East-Kent Island is situated in Grasonville, just 20 miles from Annapolis Harbor and 30 miles from Baltimore-Washington International Airport, offering easy access to both bustling city life and the tranquil beauty of Kent Narrows. The hotel has received very good user ratings for cleanliness and an excellent rating for its location.
The hotel features 25 square metre rooms with one bedroom and one bathroom, each with a range of modern amenities. Guests can enjoy a variety of activities, including swimming in the seasonal outdoor pool, relaxing in the garden, and dining at the on-site restaurant and bar, as well as taking advantage of the fitness centre and tennis court.

This five-bedroom Queenstown holiday home is situated 3.7km from Wye Oak State Park and within 9.6km of both the Queenstown Premium Outlets and Queenstown Harbour Golf Links.
This spacious 217 square metre property boasts three bathrooms, sleeps eight guests, and includes a fitness centre, spa, garden, terrace, and fully equipped kitchen with dishwasher – perfect for families.

This waterfront property in Chester, Maryland's Eastern Shore, is located less than 5 kilometres from a large shopping centre, offering easy access to amenities.
The two-bedroom, two-bathroom house sleeps eight guests and boasts a private dock, hot tub, sunroom with 270-degree waterfront views, fully equipped kitchen, and large garden with fire pit.

This Kent Island holiday home in Chester, Maryland, is minutes from the Chesapeake Bay Bridge and Annapolis, offering easy access to historical sites like the Hammond-Harwood House and John Smith House.
The 188-square-metre property sleeps eight guests in three bedrooms and three bathrooms, boasting a kitchen with fridge, microwave, and dishwasher, plus a terrace, air conditioning, parking, and stunning Cox Creek water views.

This charming cottage is located just 1.6 kilometres from the centre of Centreville, offering easy access to the town's shops, restaurants, and attractions. The property has received excellent ratings for its cleanliness, location, and overall experience.
The cottage has two bedrooms, one bathroom, and can comfortably accommodate up to five guests. It features a private, fenced-in yard, a fully equipped kitchen, air conditioning, and parking.

This Stevensville waterfront farmhouse, situated on a 35-hectare estate with pier access for boating and crabbing, is conveniently located 8 kilometres from Kent Island's restaurants and bars and 24 kilometres from Annapolis.
The three-bedroom property, sleeping up to eight guests, boasts a fully equipped kitchen, air conditioning, Wi-Fi, smart TVs, and a private 0.4-kilometre driveway ideal for children's play, offering a modern and comfortable stay.

This waterfront property, near Centreville, Maryland, is approximately 67 kilometres from Baltimore-Washington International Airport and offers private beach and dock access.
This five-bedroom, five-bathroom house boasts 260 square metres of floor space, sleeps 19 guests, includes a swimming pool, free Wi-Fi, and parking, and is pet-friendly.

This waterfront holiday home is located in Rock Hall, just a short distance from The Mainstay, Rock Hall Harbor, and Waterman’s Museum, with Ferry Park also nearby. The property has received excellent ratings for user experience, location, and cleanliness.
This charming house offers one bedroom and can accommodate up to seven guests. Enjoy a range of amenities, including a fully equipped kitchen, a terrace, a garden, and parking. You can also take advantage of the waterfront location for fishing, kayaking, or simply relaxing by the shore.

This Grasonville Cape Cod-style property enjoys direct waterfront access to the Chester River and Winchester Creek, offering proximity to restaurants and shops, and is within easy driving distance (approximately 20-30km) of St Michaels and Chestertown.
The two-bedroom, one-bathroom house sleeps five guests and boasts a full kitchen, private screened porch, private pier with kayaks and paddleboard, fire pit, and private beach area, ideal for exploring the Chester River and Winchester Creek.

Twin Ponds Lodge is situated in Centreville, just a short drive from the Queenstown Harbor Golf Links and Golf Club, offering a peaceful retreat on the Corsica River. The lodge has received excellent reviews from previous guests.
This 5-bedroom, 4-bathroom lodge can accommodate up to 15 guests, making it ideal for large families or groups. The lodge boasts a private pier, a game room, a bar, a tennis court, and plenty of outdoor space for relaxation and entertainment.

This Queenstown waterfront property offers stunning lake access, situated 4.8km from Queenstown Premium Outlets and Queenstown Harbour Golf Links, and 9.6km from Queenstown Harbour Golf Club and Wye Oak State Park.
The 340 square metre house boasts four bedrooms, four bathrooms, and sleeps eleven, featuring a private pool, tennis court, and a fully equipped kitchen alongside a games room.

This luxurious retreat is situated on the beautiful Wye River in Grasonville, Maryland, just 64 kilometres from Annapolis and St. Michaels, offering a peaceful escape in a stunning natural setting. This property has received excellent ratings for location, cleanliness, and user experience.
This spacious house has seven bedrooms and eight bathrooms, accommodating up to sixteen guests. It boasts a fully-equipped kitchen, a private pool, a tennis court, a pier, and a boat ramp, providing plenty of space for relaxation and entertainment.

This spacious Chester house, located on Kent Island, offers easy access to the waterfront, local wineries, and nature trails.
The 1000 square metre property boasts three bedrooms, three bathrooms, sleeps seventeen guests, includes a fully equipped kitchen, air conditioning, free parking and Wi-Fi, plus a billiards table.

This Grasonville holiday home is situated approximately 18 kilometres from the Chesapeake Bay Exploration Center, offering easy access to Annapolis and other attractions within a 48-kilometre radius.
This five-bedroom property boasts 418 square metres of floor space, comfortably accommodating up to 19 guests, and includes a private swimming pool, spa, and on-site boat dock with direct water access.

This waterfront house in Rock Hall offers direct Chesapeake Bay views, situated 3.7 kilometers from the Historical Society of Kent County Maryland and the Eastern Neck National Wildlife Refuge.
This six-bedroom property accommodates up to ten guests, featuring a private deck at the water's edge, an inground swimming pool, and two living rooms with electric fireplaces.

This bayfront flat in Chester, Maryland, offers direct water access and bay views, situated a short distance from Queenstown Premium Outlets and Matapeake State Park.
This property accommodates up to eight guests across four bedrooms and features a private hot tub, a boat dock, and a dedicated game room with a pool table.

The Eagles Nest property in Grasonville, Maryland, is situated approximately 27 kilometres from Sandy Point State Park, 39 kilometres from the United States Naval Academy, and 40 kilometres from Annapolis.
This five-bedroom house boasts a private pool, four bathrooms, free Wi-Fi, and parking, comfortably accommodating up to 27 guests and offering self-catering facilities in its fully equipped kitchen.

This Grasonville waterfront property, a spacious four-bedroom farmhouse near Queenstown, Maryland, boasts a private dock on Sadler's Cove offering Chesapeake Bay views, and is within 16km of Annapolis and St. Michaels.
The 264 square metre house, sleeping up to eleven guests, features a fully equipped kitchen, multiple smart TVs, a fenced garden, firepit, and propane grill, alongside high-speed internet access, making it ideal for families or groups.

This luxurious six-bedroom waterfront property, situated on a 23-hectare private estate in Rock Hall, Maryland, boasts a private beach on the Chesapeake Bay and is 5 km from Rock Hall's Main Street, offering easy access to shops, restaurants, and the Waterman's Museum.
The 465-square-metre house features four bathrooms, accommodates up to 14 guests, and includes a game room, bar, spacious porch, and access to various water activities such as crabbing, fishing, and kayaking; the Eastern Neck National Wildlife Refuge is also within cycling distance.

This Stevensville waterfront property offers direct access to Love Point State Park, is under 10km from Paul Reed Smith Guitars, and less than 14km from Matapeake State Park and the Chesapeake Bay Exploration Center.
The four-bedroom, four-bathroom house sleeps up to 14 guests and boasts a fully equipped kitchen, balcony, garden, spa, and parking; enjoy free Wi-Fi, barbecue facilities, and a smoke-free environment.

This waterfront cottage in Stevensville, Maryland, offers direct access to the Chester River and is within a few kilometres of Queenstown Harbour Golf and Bay Hills Golf Club.
This property features two bedrooms, one bathroom, and accommodates up to six guests with a pullout sofa, offering a spacious living area, a large deck, and ample yard space for outdoor activities, with fishing lights on a 250-foot pier.

This Grasonville creek-side property, a 264 square metre (2842 square feet) ranch-style house, boasts a private dock, and is located 40 kilometres from Annapolis Harbour and 24 kilometres from Sandy Point State Park.
The four-bedroom, three-bathroom dwelling sleeps thirteen guests, offering a fully equipped kitchen, free Wi-Fi, garden, parking, and is within easy driving distance of the United States Naval Academy and the Annapolis Academy of the Arts.

This Chesapeake Bay farmhouse, situated in Queenstown, Maryland's Eastern Shore, offers seclusion yet is a short drive from Eastern Shore attractions.
Sleeping up to 11 guests, this four-bedroom property boasts a fully equipped kitchen, formal dining room, wine bar, high-speed internet (500 Mbps), and direct access to Sadler's Cove for kayaking or canoeing; pets are welcome (additional charges apply).

This updated four-bedroom house in Grasonville, Maryland, offers a prime location on Kent Island, providing easy access to the Bay Bridge and a short 500-metre walk to the Chesapeake Bay, with local amenities such as waterfront restaurants and golf courses nearby.
This spacious property accommodates up to eight guests and features a private wooded lot with a large deck, a home theatre, a gym, and a putting green, alongside a first-floor master bedroom and a dedicated workspace.

This three-bedroom, two-bathroom holiday home in Grasonville offers a country setting on 3 acres, conveniently located approximately 3.2 kilometres from local attractions and the waterfront.
This spacious, accessible property accommodates up to eight guests with a split-bedroom layout, a sitting/exercise room with a queen pull-out bed, a private fenced pet area, an outdoor sport court, a covered deck with a fire pit and grills, an inside bar, a game room, and onsite owner assistance.