Chesapeake Bay vacation rentals
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Top-rated vacation rentals in Chesapeake Bay
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Home in Chestertown
4.94 out of 5 average rating, 127 reviewsCHESAPEAKE SUNSETS
Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.
Aug 7 – 14
Farm stay in Madison
4.98 out of 5 average rating, 159 reviewsMadison Nature Getaway
We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.
Oct 22 – 29
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 292 reviewsHistoric St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.
Oct 5 – 12
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Bay vacation rentals
Chesapeake Bay waterfront vacation rentals
Cottage in Onancock
4.97 out of 5 average rating, 191 reviewsWaterfront romantic getaway Eastern Shore w dock
Sep 26 – Oct 3
Farm stay in Onancock
4.99 out of 5 average rating, 167 reviewsPrivate romantic pet friendly waterfront cottage
Nov 24 – Dec 1
Cottage in Westover
4.99 out of 5 average rating, 178 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Dec 7 – 14
Guesthouse in Stevensville
5.0 out of 5 average rating, 202 reviewsWaterfront Getaway - View of bay from your bed
Apr 17 – 24
Farm stay in Chestertown
4.93 out of 5 average rating, 121 reviewsBlue Heron Farm Waterfront Chalet
Dec 17 – 24
Cottage in Heathsville
4.94 out of 5 average rating, 175 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Jan 18 – 25
Cottage in Leonardtown
4.97 out of 5 average rating, 120 reviewsBeach Front and 'Perfectly Placed'
Oct 9 – 16
Home in Reedville
4.97 out of 5 average rating, 115 reviewsSunkissed Cottage-private, natural waterfront home
Sep 6 – 13
Cottage in Kinsale
4.95 out of 5 average rating, 187 reviewsGreat little cottage with a "Rivah" view
Feb 18 – 25
Guest suite in Berlin
4.97 out of 5 average rating, 527 reviewsAyers Creek Carriage House
Apr 18 – 25
Cottage in Saint Michaels
4.99 out of 5 average rating, 136 reviewsLa Casita on Harris Creek, St. Michaels
Aug 1 – 8
Cottage in Saint Leonard
4.99 out of 5 average rating, 101 reviewsCaptain Jack's Bay Hideaway
Oct 25 – Nov 1
Chesapeake Bay fishing vacation rentals
Apartment in Frederica
4.96 out of 5 average rating, 253 reviewsSmokefree Lakeside Relaxation
Dec 16 – 23
Tiny home in Cape Charles
4.98 out of 5 average rating, 268 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Dec 30 – Jan 6
Cabin in Lusby
4.91 out of 5 average rating, 203 reviewsPeaceful Waterfront Retreat on The Bay
Oct 22 – 29
Farm stay in Cardinal
4.95 out of 5 average rating, 104 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Oct 7 – 14
Tiny home in Cambridge
4.89 out of 5 average rating, 492 reviewsBlackwater Tiny Cabin on Snakehead Creek
Jul 7 – 14
Guesthouse in Saluda
4.93 out of 5 average rating, 463 reviewsWooded Cabin retreat on fresh water pond
Apr 11 – 18
Guest suite in Piney Point
4.94 out of 5 average rating, 222 reviewsSpectacular beachfront walk-out in Piney Point MD
Jul 6 – 13
Loft in Cape May Court House
4.97 out of 5 average rating, 583 reviewsQuiet Lakefront Studio - Close to the Beach
Nov 20 – 27
Guesthouse in Church Road
5.0 out of 5 average rating, 130 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
Aug 14 – 21
Guest suite in Lusby
4.99 out of 5 average rating, 299 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Mar 19 – 26
Apartment in Stevensville
4.97 out of 5 average rating, 239 reviewsBoutique by the Bay
Aug 17 – 24
Guesthouse in Lusby
4.97 out of 5 average rating, 131 reviewsCozy Lakeside Studio Retreat.
Aug 24 – 31
Chesapeake Bay cottage rentals
Cottage in Westover
4.92 out of 5 average rating, 140 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
May 10 – 17
Cottage in Gloucester
4.97 out of 5 average rating, 190 reviews"Bee Haven" Cottage Retreat
Mar 6 – 13
Cottage in Stevensville
4.94 out of 5 average rating, 130 reviewsCottage on the Bay - Kent Island
Apr 3 – 10
Cottage in Reedville
4.9 out of 5 average rating, 156 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Jan 29 – Feb 5
Cottage in Colonial Beach
4.93 out of 5 average rating, 177 reviewsCozy cottage 3 blocks from beach
Jan 13 – 20
Cottage in Norfolk
4.98 out of 5 average rating, 263 reviewsLovely Ocean View Cottage
Feb 5 – 12
Cottage in Leonardtown
4.91 out of 5 average rating, 148 reviewsPotomac Vista Cottage at Little Pond
Aug 16 – 23
Cottage in Urbanna
4.99 out of 5 average rating, 134 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Oct 14 – 21
Cottage in Leonardtown
4.93 out of 5 average rating, 193 reviewsPotomac River Freedom Cottage
Sep 9 – 16
Cottage in Gloucester Courthouse
4.99 out of 5 average rating, 192 reviewsHistoric Ware River Cottage at Glebefield
Jan 12 – 19
Cottage in Ashland
4.95 out of 5 average rating, 240 reviewsThe Cottage at Walnut Shade
Jun 12 – 19
Cottage in Edgewater
4.99 out of 5 average rating, 123 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Jan 21 – 28
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