Beach house vacation rentals in Chesapeake Bay
Find and book unique beach houses on Airbnb
Top-rated beach house rentals in Chesapeake Bay
Guests agree: these beach houses 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 beach house rentals
Beachfront house rentals
Home in Deltaville
5.0 out of 5 average rating, 104 reviews"No Bad Days" in this Fabulous Beachhouse w/ Dock!
Dec 15 – 22
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
Jan 20 – 27
Home in Milton
4.99 out of 5 average rating, 191 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Feb 6 – 13
Home in Kent Narrows
5.0 out of 5 average rating, 280 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Home in Cambridge
4.89 out of 5 average rating, 111 reviewsDorothy's Chesapeake Delight
Oct 19 – 26
Home in Colonial Beach
5.0 out of 5 average rating, 200 reviewsBeach Blonde Cottage
Feb 7 – 14
Home in Grasonville
4.94 out of 5 average rating, 226 reviewsRiver Front, Private Single Family Home
Oct 18 – 25
Home in Deltaville
4.97 out of 5 average rating, 142 reviewsTeenie House in Deltaville
Oct 6 – 13
Beach house rentals with a pool
Home in Montross
4.93 out of 5 average rating, 167 reviewsThe Glebe
Dec 4 – 11
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Jan 28 – Feb 4
Home in Rehoboth Beach
4.99 out of 5 average rating, 119 reviewsSecluded beach beauty with private, heated pool
Sep 14 – 21
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul 16 – 23
Home in Cape May
4.97 out of 5 average rating, 260 reviews500ft to Private Beach! Fireplace, Local Pool
Dec 4 – 11
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 24 – Dec 1
Home in Ocean City
4.94 out of 5 average rating, 221 reviewsMad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Apr 5 – 12
Home in Ocean City
4.98 out of 5 average rating, 109 reviewsStunning Bayview Home with Own Private Pool
Dec 23 – 30
Private beach house rentals
Home in North
5.0 out of 5 average rating, 40 reviewsThe Llama House
Apr 9 – 16
Home in Hampton
4.92 out of 5 average rating, 13 reviewsTiny Blue Beach House
Dec 10 – 17
Home in Machipongo
5.0 out of 5 average rating, 33 reviewsPrivate Country Beach Retreat
Dec 23 – 30
Home in Fishing Creek
5.0 out of 5 average rating, 20 reviewsFishing Creek waterfront cottage
Dec 2 – 9
Home in Norfolk
5.0 out of 5 average rating, 25 reviewsStylish Beach House, Hot Tub, Pet Friendly
Feb 2 – 9
Home in Kilmarnock
5.0 out of 5 average rating, 38 reviewsSecluded beach front cottage on the Chesapeake Bay
Jan 18 – 25
Home in Stevensville
5.0 out of 5 average rating, 10 reviewsBeachside Dream
Sep 26 – Oct 3
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsRiver Cottage, Chestertown
Sep 27 – Oct 4
Destinations to explore
- House rentals United States
- Beach house rentals Virginia Beach
- House rentals Virginia Beach
- House rentals Ocean City
- Beach house rentals Ocean City
- House rentals Richmond
- Pet-friendly rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Monthly Rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- 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