Cottage vacation rentals in Chesapeake Bay
Find and book unique cottages on Airbnb
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 Reedville
4.91 out of 5 average rating, 143 reviews"Dragonfly" Waterfront Cottage on Chesapeake Bay
Aug 27 – Sep 3
Cottage in Lower Township
5.0 out of 5 average rating, 146 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
Mar 26 – Apr 2
Cottage in North Beach
4.96 out of 5 average rating, 274 reviewsWaterfront Cottage Near Herrington and North Beach
Aug 11 – 18
Cottage in Hamilton
4.94 out of 5 average rating, 309 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Nov 5 – 12
Cottage in Chesapeake
4.95 out of 5 average rating, 111 reviewsThe Cottage @ Captain Genes - Secluded Waterfront
Dec 19 – 26
Cottage in Lancaster
4.97 out of 5 average rating, 525 reviewsQuiet Cottage - Hot Tub and Creek mins from City
Nov 27 – Dec 4
Cottage in Downingtown
4.97 out of 5 average rating, 127 reviewsThe Cottage at Marsh Creek
Sep 19 – 26
Cottage in Norfolk
4.94 out of 5 average rating, 113 reviews110 Year Old Beach Carriage House @ Poseidon 902CH
Aug 13 – 20
Pet-friendly cottage rentals
Cottage in Kinsale
4.95 out of 5 average rating, 196 reviewsGreat little cottage with a "Rivah" view
Oct 21 – 28
Cottage in Saint Michaels
4.98 out of 5 average rating, 177 reviewsThe Little Anchor Cottage, St. Michaels, MD
Jan 21 – 28
Cottage in Powhatan
4.93 out of 5 average rating, 211 reviewsHorse Farm 1 nights/pets($75 Sun-Thu$145 Fri/Sat)
Jun 9 – 16
Cottage in Reedville
4.95 out of 5 average rating, 114 reviewsBull Neck Cottage
Sep 13 – 20
Cottage in Onancock
4.96 out of 5 average rating, 138 reviewsA "True" Chesapeake Bay Waterfront Experience!
Sep 6 – 13
Cottage in Berlin
4.99 out of 5 average rating, 120 reviewsBayfront Cottage w/ Amazing Views
Feb 6 – 13
Cottage in Midland
4.97 out of 5 average rating, 129 reviewsThe Stoney Cottage Hideaway
Dec 23 – 30
Cottage in Jarratt
4.93 out of 5 average rating, 190 reviewsSmith’s Cottage
Aug 17 – 24
Private cottage rentals
Cottage in Irvington
4.99 out of 5 average rating, 150 reviewsPeaceful Haven
Dec 28 – Jan 4
Cottage in Urbanna
4.99 out of 5 average rating, 134 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Oct 25 – Nov 1
Cottage in Ashland
4.95 out of 5 average rating, 247 reviewsThe Cottage at Walnut Shade
Oct 17 – 24
Cottage in Saint Michaels
4.98 out of 5 average rating, 428 reviewsSt. Michaels-Historic Dist. Margaret Wells House
Apr 4 – 11
Cottage in Leonardtown
4.93 out of 5 average rating, 194 reviewsPotomac River Freedom Cottage
Oct 10 – 17
Cottage in North
4.96 out of 5 average rating, 112 reviewsThe Nook; Peaceful 2 bedroom cottage by the bay
Dec 6 – 13
Cottage in Chincoteague Island
4.97 out of 5 average rating, 331 reviewsOnce Upon A Tide
Feb 11 – 18
Cottage in Edgewater
4.99 out of 5 average rating, 130 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Nov 22 – 29
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom