Cottage vacation rentals in Chesapeake Bay

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Top-rated cottage rentals in Chesapeake Bay

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Guest favorite

Cottage in Heathsville

4.94 out of 5 average rating, 180 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).

Sep 7 – 14

G$25,517 GYD per night

Guest favorite

Cottage in Leonardtown

4.91 out of 5 average rating, 150 reviews

Potomac Vista Cottage at Little Pond

Charming 2 Bedroom 2 Bath located 20 ft from the Maryland Potomac Shore with expansive views across the river to Virginia! Relax to the sound of the waves breaking on the revetment. Easy Access to Historic St. Mary's City and Patuxent River Naval Air Station. The Potomac Vista Cottage, a perfect getaway from the stressed and fast paced city life, Has 1000 ft of living area furnished 2 Bedroom, 2 Bathroom, Great Room, Kitchenette, Laundry and a cozy deck with a beautiful view of the River.

Nov 13 – 20

G$33,479 GYD per night

Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 126 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.

Nov 6 – 13

G$37,690 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 195 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan 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 and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Jan 9 – 16

G$18,506 GYD per night

Guest favorite

Cottage in Ashland

4.95 out of 5 average rating, 247 reviews

The Cottage at Walnut Shade

You won’t have to travel far outside of Richmond to find relaxation in the countryside! Convenient to I-95, the Cottage at Walnut Shade provides fully furnished privacy and a chance to escape among the farm fields and history of Hanover county. Whether you’re a biker, hiker, history nut, beer fanatic, theatre lover or just want a place to call your own for the weekend, you may be surprised to find it all in the town of Ashland and surrounding Hanover county. *Internet is now available*

Aug 27 – Sep 3

G$24,926 GYD per night

Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 182 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to 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 Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Apr 11 – 18

G$77,339 GYD per night

Guest favorite

Cottage in Gloucester

4.97 out of 5 average rating, 196 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.

Sep 27 – Oct 4

G$25,883 GYD per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 138 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Oct 25 – Nov 1

G$111,605 GYD per night

Guest favorite

Cottage in Onancock

4.97 out of 5 average rating, 198 reviews

Escape to the Eastern Shore - Upscale Waterfront

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles

Nov 24 – Dec 1

G$37,630 GYD per night

Guest favorite

Cottage in Gloucester Courthouse

4.98 out of 5 average rating, 195 reviews

Historic Ware River Cottage at Glebefield

Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.

Apr 21 – 28

G$34,741 GYD per night

Guest favorite

Cottage in Westover

4.92 out of 5 average rating, 142 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

This Chesapeake Bayfront cottage has spectacular views to take you away from everything in any season. It boasts more than 120 feet of waterfront, and you can dangle your feet off the 70 ft “dock of the bay”. Launch kayaks from the small sandy beach in summer, or cozy up to the wood stove in the winter. Inside, you’ll find wood floors throughout, modern kitchen & baths with bay views from every room. Kayaks, SUP, bicycles & crab traps too!

Apr 27 – May 4

G$48,714 GYD per night

Guest favorite

Cottage in White Stone

4.91 out of 5 average rating, 300 reviews

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Nov 27 – Dec 4

G$25,078 GYD per night