Holiday houses in Queen Anne

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Top-rated holiday rentals in Queen Anne

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Guest favourite
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
4.93 out of 5 average rating, 109 reviews

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.

Guest favourite
A serene view of a calm lake is captured from a private deck. Surrounding trees reflect gently in the water, creating a soothing landscape under soft morning light. A table and two chairs sit on the deck, inviting relaxation and enjoyment of the natural scenery.
Guesthouse in Wye Mills
4.92 out of 5 average rating, 36 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.

Top Guest favourite
The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.
Apartment in Greenwood
4.97 out of 5 average rating, 633 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Top Guest favourite
A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.
Apartment in Chestertown
4.96 out of 5 average rating, 254 reviews

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Top Guest favourite
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
4.99 out of 5 average rating, 630 reviews

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.

Top Guest favourite
Home in Centreville
5 out of 5 average rating, 48 reviews

Lansdowne Manor | Firepit | BBQ | Pets | 198 Mbps

Historic country manor located in a private tranquil setting, surrounded by mature trees & nature. ★ "An absolutely amazing property—graceful, historical, and very well cared for." ☞ Deck w/ BBQ + fire pit + dining ☞ Spacious backyard w/ lush views ☞ Fully equipped + stocked kitchen ☞ Parking → driveway (4 cars) ☞ Onsite washer + dryer ☞ 55” + 43” smart TVs ☞ 198 Mbps wifi ☞ Pet friendly 9 mins → DT Centreville (cafes, dining, shopping) 13 mins → Tuckahoe State Park hiking trails

Guest favourite
A historic row of four identical houses is displayed, featuring charming yellow siding and brown roofs. Each unit boasts a small porch with steps leading up to the entrance. A lush green lawn surrounds the homes, highlighting the natural beauty of the area.
Cottage in Centreville
4.93 out of 5 average rating, 57 reviews

Captain’s Quarters - Unique home on Corsica River!

The Captains Quarters was built in 1880 by local waterman, Captain John H. Osman. The Captain built 4 identical houses for the Captains of his fleet to enjoy. The Captains Quarters is registered with the Maryland National Historical Trust. This unique and cozy home takes you back in time, all while enjoying all of the modern amenities. Our guests can expect to enjoy coffee on the patio overlooking the Corsica River, games and a bar in the brick floor basement and tons of relaxation!

Top Guest favourite
A cabin nestled among tall trees presents a rustic appearance. A flowering garden features pink blooms and lush greenery, complementing a wooden fence. The cabin's dark exterior contrasts with the vibrant natural surroundings, creating a serene atmosphere.
Cabin in Greenwood
4.93 out of 5 average rating, 14 reviews

Mast Cabin

Enjoy a peaceful stay in our cabin set in the edge of the woods. The cabin is 100 feet from our house, and has its own gravel driveway along the woods. We are located in a rural area on 8 acres . You are welcome to explore and enjoy our property. We are located 30 miles from Delaware beaches. When requesting to book, please include a brief message telling us who is coming (max 2 guests) and the purpose for your travel plans. Requests without this basic info won’t be approved.

Top Guest favourite
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
4.96 out of 5 average rating, 112 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.

Guest favourite
A single-family home with a brick exterior is surrounded by greenery. The inviting front porch is complemented by a stone pathway leading to a spacious outdoor seating area, featuring a fire pit and chairs for relaxation.
Bungalow in Queen Anne
4.94 out of 5 average rating, 88 reviews

Private bungalow with fire pit near Easton, Denton

- High-speed Internet - Premium Samsung washer and dryer - Fire Pit - Level 2 EV Charger - Two (2) cruiser bicycles - Memory foam mattresses - Full kitchen - Smart TV - Quiet, secluded space with easy access - 5 minutes to Denton - 15 minutes to Easton - 15 minutes to Centreville - 30 minutes to St. Michaels Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure.

Superhost
A living area is highlighted by original wood flooring, with a circular wooden table at its center. A dark leather sofa and two green patterned chairs provide seating. Natural light enters through multiple windows, and a wooden entertainment center holds a television.
Home in Centreville
5 out of 5 average rating, 6 reviews

| Eastern Shore | Family Getaway

Visit the beautiful Eastern Shore of Maryland and enjoy all the activities it has to offer! The house is just a couple of miles from the Wye River where you can launch your boat or rent a motor or row boat there! Near the historic towns of Centreville, Chestertown, Easton and Saint Michael's, known as 'The Hamptons of DC' with fine dining a museum, winery and brewery all on a historic main street.

Top Guest favourite
A cozy living area features a brown leather sofa next to a white coffee table. A decorative rug with star patterns lies on the floor. A green potted plant adds a natural touch, complemented by a television on a media unit. Light enters from the window.
Apartment in Chester
4.97 out of 5 average rating, 276 reviews

Cozy Waterfront Apartment Chester, MD

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. WiFi included. Private porch to enjoy water view!

Popular amenities for Queen Anne holiday rentals