Beachfront holiday rental in Queen Anne's County

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Top-rated beachfront accommodation in Queen Anne's County

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Top Guest favourite

Home in Chester

5 out of 5 average rating, 34 reviews

*Waterfront Sunset Bayview* sleeps 6

Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent direct sunset views, that force you to stop and take it in! Our open-concept home is tastefully decorated with a blend of modern amenities and cozy charm, complete with large windows that allow natural light to fill the space along with stunning views of the Bay. Escape the hustle of everyday life and immerse yourself in the serene beauty from the comfort of your private retreat.

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Cottage in Grasonville

4.89 out of 5 average rating, 62 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

**Close to all the Wedding Venues** Come relax at the all new Coastal Haven Cottage. Take a nice morning walk to the beach &enjoy your coffee while sitting on a bench overlooking the Chesapeake Bay. Light, bright coastal feel inside the home & enjoy the wonderful outdoor space on the deck or in an Adirondack chair around the firepit. Great outdoor dining space to enjoy crabs or burgers & large yard for the kids to run. 3 Min Drive to The Jetty & many restaurants or walk along the new Boardwalk.

Top Guest favourite

Home in Grasonville

4.95 out of 5 average rating, 268 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

Guest favourite

Guesthouse in Rock Hall

4.95 out of 5 average rating, 21 reviews

The Birdhouse on Swan Creek, Welcome!

An adorable carriage house with panoramic views overlooking Swan Creek -- centrally located, yet private enough to be surrounded by nature. Bird watchers would have a grand time here, with frequent Bald Eagles sightings pre-summer, ospreys, and many other waterfowls at your window in summer. Centrally located: 3 blocks from town beach, restaurants across the road and Rock Hall downtown within walkable distance, next to two local marina. Your private dock through Blue Heron Marsh to Swan Creek.

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Home in Chester

4.78 out of 5 average rating, 9 reviews

Crab Alley Bay House, Waterfront Home w Hot Tub

This waterfront home in located on an inlet off of Crab Alley Bay on Kent Island. Located on a quiet street, the home offers privacy but is just 6 minutes drive from town and close to great local seafood restaurants. There is a public boat ramp 1/2 mile from the house to launch your boat. Guests are welcome to use the boat dock. The home offers a fully equipped kitchen, 4 BRDMS, 2 Baths, game room in the detached garage, deck overlooking the water, Blackstone & Pellet Grills, TV/WIFI, Hot Tub

Top Guest favourite

Cottage in Annapolis

4.98 out of 5 average rating, 46 reviews

Charming Waterfront Cottage on Historic Property

Enjoy a peaceful get-away in a beautifully renovated, historic cottage. The 115 acre property is on a peninsula with over 2 miles of shoreline. This charming home has water access, trails, a canoe, a hammock, and a lovely grilling patio. The cottage is on the private grounds of Whitehall Mansion, built in 1764 as the home of Governor Sharpe. The farm is used for horse boarding and private weddings. Nearby attractions include Annapolis, the US Naval Academy, Washington D.C., and Baltimore.

Guest favourite

Home in Stevensville

4.96 out of 5 average rating, 49 reviews

Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House: almost 1800 sq ft. Incredible Water View home across from Kentmorr Beach Bar & Grill/Marina/Fishing Boats near Matapeake State Park & Beach. Perfect for holidays, birthdays, wedding guests, team builds, family fun, fishing, golfing, etc. 4 Bedrooms, 3 Full Baths, 4th Bedroom is large family room with big Internet TVs/fireplace plus a Kitchen, Living/Dining Area, and a huge yard with your very own private beach volleyball court and spacious deck overlooking the Chesapeake Bay.

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Home in Stevensville

4.89 out of 5 average rating, 47 reviews

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Guest favourite

Home in Stevensville

4.96 out of 5 average rating, 89 reviews

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

Guest favourite

Home in Annapolis

4.9 out of 5 average rating, 199 reviews

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Top Guest favourite

Cottage in Annapolis

4.93 out of 5 average rating, 28 reviews

Bay View Beach Cottage, perfect for long-term

A relaxing bay retreat, perfect for long- term stays. Well stocked kitchen, laundry, off-street parking, large yard with patio, comfy beds ( linens and towels included), and beautiful bay views from the cottage. Community beach (unguarded) to swim or bring your water kayaks or SUPs. Dining and grocery close by. Enjoy the bay views of boats going by, the sound of birds, and great sunsets. Minutes to Rt. 50. Close to downtown Annapolis.

Guest favourite

Holiday home in Queenstown

4.98 out of 5 average rating, 53 reviews

Heart of the Chesapeake

Enjoy 270 degrees of waterfront living on over 5 acres of land. This one of a kind property is extremely private with a large pool, private sandy beach, (brand new dock 2024 - deep water with shore power and water), pool table, outdoor dining and close to shopping outlets and restaurants. All rooms offer gorgeous views of the Wye River. The fishing is phenomenal and the wildlife is plentiful.