Cottage holiday rentals in Chesapeake Bay
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Top-rated cottage rentals in Chesapeake Bay
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Chesapeake Bay
Cottage rentals with a hot tub
Cottage in Reedville
4.91 out of 5 average rating, 149 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Cottage in North Beach
4.96 out of 5 average rating, 278 reviewsWaterfront Cottage Near Herrington and North Beach
Cottage in Lower Township
5.0 out of 5 average rating, 154 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
Cottage in Chesapeake
4.95 out of 5 average rating, 116 reviewsThe Cottage @ Captain Genes - Secluded Waterfront
Cottage in Norfolk
4.94 out of 5 average rating, 116 reviews110 Year Old Beach Carriage House @ Poseidon 902CH
Cottage in Villas
4.87 out of 5 average rating, 194 reviewsCozy Cottage~Hot Tub~Gas Fireplace~Pet Friendly!
Cottage in Rehoboth Beach
4.94 out of 5 average rating, 126 reviewsDog friendly *HOT TUB* Close to outlets, Sleeps 7
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Pet-friendly cottage rentals
Cottage in Montross
4.97 out of 5 average rating, 101 reviewsNewly Renovated 2BR Waterfront Cottage with Dock
Cottage in Berlin
4.99 out of 5 average rating, 127 reviewsBayfront Cottage w/ Amazing Views
Cottage in Onancock
4.96 out of 5 average rating, 141 reviewsA "True" Chesapeake Bay Waterfront Experience!
Cottage in Saint Michaels
4.98 out of 5 average rating, 184 reviewsThe Little Anchor Cottage, St. Michaels, MD
Cottage in Norfolk
4.97 out of 5 average rating, 275 reviewsLovely Ocean View Cottage
Cottage in Norfolk
4.98 out of 5 average rating, 182 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Cottage in Norfolk
4.97 out of 5 average rating, 206 reviewsPositano Villa
Cottage in Kinsale
4.95 out of 5 average rating, 204 reviewsGreat little cottage with a "Rivah" view
Private cottage rentals
Cottage in Urbanna
4.99 out of 5 average rating, 138 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Cottage in Stevensville
4.94 out of 5 average rating, 135 reviewsCottage on the Bay - Kent Island
Cottage in Reedville
4.95 out of 5 average rating, 118 reviewsBull Neck Cottage
Cottage in Colonial Beach
4.93 out of 5 average rating, 197 reviewsCozy cottage 3 blocks from beach
Cottage in Edgewater
4.99 out of 5 average rating, 132 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Cottage in Ashland
4.95 out of 5 average rating, 249 reviewsThe Cottage at Walnut Shade
Cottage in Leonardtown
4.93 out of 5 average rating, 196 reviewsPotomac River Freedom Cottage
Cottage in Saxis
4.87 out of 5 average rating, 206 reviewsISLAND SUNSETS Near Chincoteague Island
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