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, 274 reviewsWaterfront Cottage Near Herrington and North Beach
Jul 26 – Aug 2
Cottage in Reedville
4.91 out of 5 average rating, 143 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Jan 6 – 13
Cottage in Lower Township
5.0 out of 5 average rating, 147 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
Feb 26 – Mar 5
Cottage in Norfolk
4.94 out of 5 average rating, 113 reviews110 Year Old Beach Carriage House @ Poseidon 902CH
Oct 4 – 11
Cottage in Chesapeake
4.95 out of 5 average rating, 111 reviewsThe Cottage @ Captain Genes - Secluded Waterfront
Feb 16 – 23
Cottage in Hamilton
4.94 out of 5 average rating, 310 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Apr 23 – 30
Cottage in Rehoboth Beach
4.96 out of 5 average rating, 123 reviewsDog friendly *HOT TUB* Close to outlets, Sleeps 7
Mar 27 – Apr 3
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Jan 26 – Feb 2
Pet-friendly cottage rentals
Cottage in Kinsale
4.95 out of 5 average rating, 199 reviewsGreat little cottage with a "Rivah" view
Feb 21 – 28
Cottage in Reedville
4.95 out of 5 average rating, 114 reviewsBull Neck Cottage
May 25 – Jun 1
Cottage in Saint Michaels
4.98 out of 5 average rating, 177 reviewsThe Little Anchor Cottage, St. Michaels, MD
Mar 10 – 17
Cottage in Norfolk
4.98 out of 5 average rating, 269 reviewsLovely Ocean View Cottage
Feb 10 – 17
Cottage in Onancock
4.96 out of 5 average rating, 138 reviewsA "True" Chesapeake Bay Waterfront Experience!
Nov 8 – 15
Cottage in Jarratt
4.93 out of 5 average rating, 190 reviewsSmith’s Cottage
Dec 3 – 10
Cottage in Norfolk
4.98 out of 5 average rating, 176 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Feb 9 – 16
Cottage in Berlin
4.99 out of 5 average rating, 121 reviewsBayfront Cottage w/ Amazing Views
Dec 13 – 20
Private cottage rentals
Cottage in Stevensville
4.94 out of 5 average rating, 132 reviewsCottage on the Bay - Kent Island
Sep 29 – Oct 6
Cottage in Ashland
4.95 out of 5 average rating, 247 reviewsThe Cottage at Walnut Shade
Aug 27 – Sep 3
Cottage in Leonardtown
4.93 out of 5 average rating, 194 reviewsPotomac River Freedom Cottage
Oct 22 – 29
Cottage in Saint Michaels
4.98 out of 5 average rating, 428 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Apr 18 – 25
Cottage in Urbanna
4.99 out of 5 average rating, 135 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Oct 17 – 24
Cottage in Chincoteague Island
4.97 out of 5 average rating, 332 reviewsOnce Upon A Tide
Jan 22 – 29
Cottage in Gloucester Point
4.95 out of 5 average rating, 199 reviewsThe Cottage on Sarah's Creek
Jul 17 – 24
Cottage in Edgewater
4.99 out of 5 average rating, 130 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Jul 9 – 16
Destinations to explore
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