Chesapeake Bay vacation rentals
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Top-rated vacation rentals in Chesapeake Bay
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Popular amenities for Chesapeake Bay vacation rentals
Other great vacation rentals in Chesapeake Bay
Home in Chestertown
4.94 out of 5 average rating, 128 reviewsCHESAPEAKE SUNSETS
May 4 – 11
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Jan 1 – 8
Cabin in Deltaville
4.97 out of 5 average rating, 253 reviews"The Little Red Cabin" aka The Galley
Mar 27 – Apr 3
Cottage in Heathsville
4.94 out of 5 average rating, 178 reviewsHedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Mar 4 – 11
Guest suite in Chincoteague
4.93 out of 5 average rating, 224 reviewsBaywatch North-Waterfront & Roaming Ponies
Oct 21 – 28
Home in Reedville
4.96 out of 5 average rating, 203 reviewsWaterfront FamilyFriendly Home Improved for 2023
Apr 4 – 11
Cottage in Westover
4.99 out of 5 average rating, 181 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Feb 3 – 10
Guest suite in Colonial Beach
4.97 out of 5 average rating, 262 reviewsBayview Bungalow
Dec 11 – 18
Chesapeake Bay fishing vacation rentals
Tiny home in Cambridge
4.89 out of 5 average rating, 496 reviewsBlackwater Tiny Cabin on Snakehead Creek
Sep 23 – 30
Apartment in Frederica
4.97 out of 5 average rating, 258 reviewsSmokefree Lakeside Relaxation
Oct 27 – Nov 3
Tiny home in Cape Charles
4.98 out of 5 average rating, 273 reviewsThe Laughing King Retreat Honeymoon Island Cottage
Jan 13 – 20
Loft in Cape May Court House
4.97 out of 5 average rating, 589 reviewsQuiet Lakefront Studio - Close to the Beach
Nov 28 – Dec 5
Home in Reedville
4.97 out of 5 average rating, 118 reviewsSunkissed Cottage-private, natural waterfront home
Aug 13 – 20
Guest suite in Lusby
4.99 out of 5 average rating, 303 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Apr 1 – 8
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Apr 15 – 22
Guest suite in Arnold
4.96 out of 5 average rating, 565 reviewsOld Bay Bungalow
Jul 5 – 12
Chesapeake Bay home rentals
Home in Virginia Beach
4.9 out of 5 average rating, 207 reviewsQuilted Quarters by the Bay with Private Entrance
Nov 28 – Dec 5
Home in Lusby
5.0 out of 5 average rating, 111 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Jun 25 – Jul 2
Home in TYLERTON
4.95 out of 5 average rating, 118 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
Feb 12 – 19
Home in Chestertown
5.0 out of 5 average rating, 155 reviewsPet friendly, historic house, near town center.
Jan 18 – 25
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Mar 7 – 14
Home in Gloucester
4.95 out of 5 average rating, 133 reviewsBee Humble Cottage Entire Home
Sep 26 – Oct 3
Home in Milton
4.99 out of 5 average rating, 189 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Mar 8 – 15
Home in Shady Side
5.0 out of 5 average rating, 116 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Jan 11 – 18
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