Vacation rentals in Queen Anne

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Top-rated vacation rentals in Queen Anne

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Top guest favorite

A stately historic home is depicted from the front, showcasing a charming design with white siding and a blue front door. The property features a peaked roof and is surrounded by lush greenery, including several trees and well-maintained shrubs.

Place to stay in Denton

Turnbridge Manor - Waterfront Historic House

A waterfront property located in the heart of downtown Denton, on Maryland's Eastern Shore, the stately historic home built in the 1860’s offers modern amenities and luxurious accommodations. Guests can take in the charm of Denton from our sunny front porch or sit in the many outdoor oases to relax and enjoy the beautiful terraced grounds overlooking the tranquil Choptank River. Located less than 60 minutes to the beach, 35 minutes to historic St. Michaels and minutes to the Harriet Tubman Byway

4.95 out of 5 average rating, 101 reviews

Top guest favorite

A comfortable living room features plush seating arrangements, including reclining chairs and a spacious sofa. A coffee table sits in the center, complemented by a large television mounted above a brick fireplace. Bookshelves filled with titles line the walls, adding a cozy touch.

Home in Easton

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre

Bring the whole family to my spacious house. 3 bathrooms for everyone to get ready. 2 king beds and 2 queen beds across 4 bedrooms. Huge living room, kitchen, and dinning room. Enjoy a sun room and fenced in back yard. Fresh eggs from backyard chickens. Merry Maids regularly cleans the bathrooms and kitchen. The basement, garage, and shed are for storage, and are not part of the rental. While quiet just outside of the city, there maybe some highway noise or farm animal noise. Large driveway

4.97 out of 5 average rating, 100 reviews

Guest favorite

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

4.93 out of 5 average rating, 126 reviews

Guest favorite

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

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.

4.95 out of 5 average rating, 310 reviews

Top guest favorite

The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.

Home in Stevensville

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

4.97 out of 5 average rating, 131 reviews

Top guest favorite

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

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.

4.99 out of 5 average rating, 149 reviews

Top guest favorite

The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.

Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

4.99 out of 5 average rating, 657 reviews

Top guest favorite

A modern guest barn is situated amidst a serene farm setting, with a sleek metal roof and large windows. The exterior features a combination of wood and metal materials. Surrounding lush green fields are dotted with trees, enhancing the peaceful atmosphere.

Barn in Queenstown

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

4.99 out of 5 average rating, 85 reviews

Top guest favorite

A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.

Home in Greensboro

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.

4.97 out of 5 average rating, 144 reviews

Top guest favorite

A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.

Apartment in St. Michaels

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

4.98 out of 5 average rating, 160 reviews

Top guest favorite

Home in Centreville

Family Retreat at Historic Lansdowne Manor

Escape to Lansdowne, a historic Federal-period manor house recognized by the Library of Congress. This private, tranquil retreat offers a unique blend of vintage charm and modern comfort for up to 8 guests. Surrounded by open fields and nature, this 4 bedroom home features a fully equipped kitchen and high-speed Wi-Fi. Perfect for families and history lovers seeking a peaceful getaway just minutes from Centreville and a state park lake and trails.

5.0 out of 5 average rating, 62 reviews

Top guest favorite

Home in Chestertown

The Garden Estate: Historic Town Center Home

Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.

5.0 out of 5 average rating, 252 reviews