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Cottage rentals near Chesapeake Bay

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Top-rated cottage rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Cottage in Heathsville
4.93 out of 5 average rating, 241 reviews

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

We welcome you to stay at "HedgeRow" a deer haven on the Great Wicomico River, located in a hidden corner of the popular Northern Neck of Virginia. You'll be delighted in all the area and this charming listing has to offer. Located just 10 minutes from Kilmarnock, enjoy wineries, shopping and local attractions nearby. Bring your boat, kayaks, fishing rods or friends, then relax in all things that encompass river life. There is a boat ramp and fishing dock available for guests use (Adults Only).

Guest favourite
A charming cottage exterior showcases a well-maintained garden with colorful flowers lining the pathway. The front porch features a welcoming entrance, while large windows provide ample natural light. A white picket fence frames the lush greenery that surrounds the home.
Cottage in North Beach
4.91 out of 5 average rating, 119 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Top Guest favourite
The charming beach house features a white picket fence and a welcoming front porch. A large anchor motif is displayed prominently above the door. Surrounding greenery provides a natural backdrop, enhancing the cozy exterior aesthetics in a tranquil setting.
Cottage in Lusby
4.98 out of 5 average rating, 286 reviews

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

Guest favourite
The view from the entrance displays a spacious deck leading to the water, framed by sturdy wooden supports. Two large doors provide access and natural light, highlighting the inviting outdoor space with chairs positioned for relaxation.
Cottage in Weems
4.98 out of 5 average rating, 128 reviews

The Crab Shack

Enjoy the sunrise at this unique and tranquil getaway! This property was originally a seafood processing facility...hence The Crab Shack! Watch all the action on the water right out the front door with local waterman in and out of beautiful Carter's Creek to and from the Rappahannock River and Chesapeake Bay. There are marinas and The Tides Inn very close by. This property provides privacy and a short 10 minute drive to nearby restaurants and shops in Irvington, Kilmarnock, and White Stone.

Top Guest favourite
A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.
Cottage in Leonardtown
4.96 out of 5 average rating, 238 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Top Guest favourite
Cottage in Saint Leonard
4.94 out of 5 average rating, 173 reviews

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Fall/Winter promo: Book two nights, get one free on midweek stays (Monday thru Thursday)! Book two nights, get 50% off third night on weekend stays. Send a message after booking, and the promo night will be added. Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) Message for multi-night and monthly rates.

Top Guest favourite
A charming cottage is set against a backdrop of tall trees, showcasing a light-colored exterior. A welcoming front porch features comfortable seating and an American flag. The landscaped yard includes potted plants and a gravel pathway leading to the entrance.
Cottage in Gloucester
4.97 out of 5 average rating, 261 reviews

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Top Guest favourite
Cottage in Charlestown
4.95 out of 5 average rating, 244 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a WINTRY romantic couple's getaway! honeymoon/celebrations Designed with that in mind,a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels

Guest favourite
A serene view of a cove with gentle waves lapping against a sandy shore. The calm water reflects the clear blue sky and nearby greenery. Footprints are visible in the sand, leading toward the water's edge.
Cottage in Reedville
4.91 out of 5 average rating, 214 reviews

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

Top Guest favourite
The Gothic Revival-style cottage is showcased from its charming exterior, featuring large arched windows and a welcoming front porch. Two wooden chairs sit invitingly on the porch, complemented by seasonal decorations. Surrounding trees provide a sense of tranquility within the peaceful setting.
Cottage in Irvington
5 out of 5 average rating, 233 reviews

Peaceful Haven: nature & charming town

Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.

Top Guest favourite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover
4.99 out of 5 average rating, 245 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Top Guest favourite
A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.
Cottage in California
4.97 out of 5 average rating, 262 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

Popular amenities for cottage rentals near Chesapeake Bay

Quick stats about cottage rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 350 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $57 AUD per night before taxes and fees

  • Verified guest reviews

    Over 28,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    280 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 170 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    340 of Chesapeake Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

  • 4.9 Average rating

    Chesapeake Bay stays are highly rated by guests—averaging 4.9 out of 5!

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