Cottage vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Bay cottage rentals
Cottage rentals with a hot tub
Cottage in North Beach
4.96 out of 5 average rating, 279 reviewsWaterfront Cottage Near Herrington and North Beach
Cottage in Reedville
4.91 out of 5 average rating, 151 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Cottage in Chesapeake
4.95 out of 5 average rating, 116 reviewsThe Cottage @ Captain Genes - Secluded Waterfront
Cottage in Lower Township
5 out of 5 average rating, 155 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
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, 195 reviewsCozy Cottage~Hot Tub~Gas Fireplace~Pet Friendly!
Cottage in Rehoboth Beach
4.94 out of 5 average rating, 127 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 Saint Michaels
4.98 out of 5 average rating, 186 reviewsThe Little Anchor Cottage, St. Michaels, MD
Cottage in Norfolk
4.98 out of 5 average rating, 184 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Cottage in Kinsale
4.95 out of 5 average rating, 204 reviewsGreat little cottage with a "Rivah" view
Cottage in Norfolk
4.97 out of 5 average rating, 276 reviewsLovely Ocean View Cottage
Cottage in Onancock
4.96 out of 5 average rating, 141 reviewsA "True" Chesapeake Bay Waterfront Experience!
Cottage in Berlin
4.99 out of 5 average rating, 129 reviewsBayfront Cottage w/ Amazing Views
Cottage in Norfolk
4.97 out of 5 average rating, 207 reviewsPositano Villa
Cottage in Glen Burnie
4.92 out of 5 average rating, 148 reviewsHome away from home
Private cottage rentals
Cottage in Reedville
4.95 out of 5 average rating, 118 reviewsBull Neck Cottage
Cottage in Urbanna
4.99 out of 5 average rating, 139 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Cottage in Colonial Beach
4.93 out of 5 average rating, 198 reviewsCozy cottage 3 blocks from beach
Cottage in Edgewater
4.99 out of 5 average rating, 133 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Cottage in Irvington
4.99 out of 5 average rating, 152 reviewsPeaceful Haven - pool, greenery, charming town
Cottage in Saxis
4.87 out of 5 average rating, 207 reviewsISLAND SUNSETS Near Chincoteague Island
Cottage in Saint Michaels
4.98 out of 5 average rating, 437 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Cottage in North
4.96 out of 5 average rating, 117 reviewsThe Nook; Peaceful 2 bedroom cottage by the bay
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