Cottage holiday rentals in Chesapeake Bay

Find and book unique cottages on Airbnb

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Popular amenities for Chesapeake Bay cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Annapolis
4.87 out of 5 average rating, 83 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

ChelseaRating, 5 stars3 days ago
The host was very kind, accommodating, and had a quick response time to all messages. The house is adorable and was a great fit for 5 friends wanting to get away for a night! I would highly recommend this house and encourage you to use the outdoor space!
Guest favourite
Cottage in Saint Leonard
4.96 out of 5 average rating, 136 reviews

Block to Beach, Screened deck, Hot Tub, No CF

AuroraRating, 5 stars3 weeks ago
Loved our stay here! It was cozy and peaceful for a little weekend getaway. While it was rainy we still had a lovely view of the water and stuff to do nearby (recommend the antiques marketplace). Kelcey was helpful and communicative! Want to come back to read on that beautiful screened porch!
Top Guest favourite
Cottage in Lower Township
5 out of 5 average rating, 218 reviews

Octopus Cottage: Hot Tub | Kayaks | Fire Pit

KirstenRating, 5 stars5 days ago
The cottage is adorably cute & could not have been more clean. I loved that it is right next to the beach, just a few steps away. I wasn't traveling during beach season, so I don't know if it's a swimming beach - you will want to check that out before you go if that's important to you - but it was nice to walk, & the sunset over the water was glorious. There didn't appear to be much in the way of things to do right in the town, but it's a short drive to lovely Cape May. The hot tub was a delight - albeit not super private, as a picket fence & shrubbery block it from the road. When you're in the hot tub you can't be seen, but when you stand up to get out of it, you can view the road. That being said, it's not a busy road. The house between the cottage & the beach (the owner's house) is gorgeous, but the house across the street on the other side leaves a little bit to be desired. However, as a woman traveling alone, I felt very safe. And Donna brought delicious homemade muffins. LOVED!!
Guest favourite
Cottage in Hamilton
4.95 out of 5 average rating, 373 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

CalvinRating, 5 stars3 weeks ago
This place is absolutely beautiful! It was impeccably clean and offered stunning views! The night was wonderfully quiet, making it feel like we were in our own serene world. The layout of the space is amazing, and to top it off, there’s a delightful winery “Firefly” just a short 20-foot walk away! The hot tub was the perfect addition, providing a relaxing way to unwind while enjoying the views. We couldn't have asked for a better stay!
Guest favourite
Cottage in Charlestown
4.96 out of 5 average rating, 165 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Joseph & TracyRating, 5 stars1 week ago
The property is beautiful, its just like the pictures. The location is peaceful and quite. Its a perfect spot to just to relax and reconnect. Can't say enough good things about the cottage. Clean, Bed was nice, view was amazing, Hot tub, kayaks, plenty of firewood for a beach fire. During our stay we went to main street in North East it was about a 7 minute drive. It was a nice little town to walk. Chesapeake Coffee Co for a breakfast sandwich and a coffee. We had lunch at Woody's crab shack. Ordered in pizza from Bella Pizza, Went to Nauti Goose. I was underwhelmed at all restaurants and by all meals. If we come back again, I'd get groceries to cook, there is a grill to use (we didn't) and stay in, just take in the view and enjoy the peaceful waves. We would defiantly recommend and hopefully be back again soon.
Guest favourite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 167 reviews

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

MikeRating, 5 stars1 week ago
This was a great place to stay and was exactly what we expected. The house is set in a residential neighborhood, but felt private. Definitely have to drive to get to the beaches, but it was not far (maybe 10 minutes, more during the busy season, I'm sure). Everything was clean. Check in was simple and easy. They do not bug you, and since everything was simple, I had no reason to contact them. Dog friendly, but so clean you wouldn't know. Fenced in back yard was perfect for your dog. Plenty of indoor and outdoor seating area - although, 7 adults might be pretty cramped. Maybe 2 families max. Will definitely stay here again.
Guest favourite
Cottage in Norfolk
4.91 out of 5 average rating, 109 reviews

Cozy Cottage - NEW hot tub, dogs OK, fenced yard

GraceRating, 5 stars1 week ago
The house was super clean, comfortable and walking distance to some delicious restaurants! I highly recommend this spot if you have dogs; the yard is fully fenced with privacy fencing, is clean and spacious enough for large dogs to run around. It’s in a very quiet neighborhood as well. I’ve stayed in some other Airbnb’s that had a chore list a mile long, with complicated check in/out instructions but this place was the total opposite. The whole process and stay was super easy and worry free. We’ll definitely be booking again in the future! :)
Guest favourite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 176 reviews

Hot Tub, Fire Pit, Private Back Yard, Relaxing

MatthewRating, 5 stars2 weeks ago
Laura and Red were great, the ice maker was not working properly before we arrived and they dropped off a bag of ice to tide us over until the machine was back online. The location is great, close to everything and also easy to get to. If you know Rehoboth, you know it can be complicated when you need to make u-turns every time you want to go somewhere. This house has easy access to a grocery store without having to get on 1. Hot tub was super clean and there are shocks provided to keep it that way through the week. Nice touches like sound machines in all of the bedrooms to drown out any outside noise. Great spot!!

Pet-friendly cottage rentals

Guest favourite
Cottage in Wildwood Crest
4.91 out of 5 average rating, 186 reviews

Cozy Cottage 1.5 Blocks from Beach; Pet Friendly!

JenniferRating, 5 stars2 days ago
My family absolutely loved our stay. Peter was responsive and helpful. Check in was easy and we felt right at home. Great location, very close to the beach.
Guest favourite
Cottage in Annapolis
4.93 out of 5 average rating, 200 reviews

Secluded Cottage_ A+ Amenities in Historic Dwntwn

EricRating, 5 stars1 month ago
Jennifer's cottage is great! It is quiet, peaceful, and private but still right in the middle of everything - a 30 second walk to coffee shops, restaurants, bars, etc. Would also be really convenient for folks visiting the Naval Academy or St Johns. We had a great time and will almost certainly be back.
Guest favourite
Cottage in Lewes
4.87 out of 5 average rating, 201 reviews

BnB’s Dog-Friendly Cottage

SydneyRating, 5 stars2 weeks ago
Jacki's home was so lovely and perfect for a weekend getaway with some friends. We brought our dog who absolutely loved the fenced-in yard and extra loved the mountain of toys stocked in the house!
Guest favourite
Cottage in Cape May
4.9 out of 5 average rating, 248 reviews

House on the Hill- Dog Friendly Near Cape May

KaitlynRating, 5 stars3 weeks ago
Beautiful and clean home that is extremely close to everything you’d like to do in Cape May! Ellen responds quickly to any questions you may have. We had a great weekend!
Top Guest favourite
Cottage in Norfolk
4.97 out of 5 average rating, 326 reviews

Lovely Ocean View Cottage

MargoRating, 5 stars2 days ago
We had a wonderful stay with our puppy! Chuck was very thoughtful and welcoming with the many amenities available. We felt right at home and it's so close to restaurants and the water. Looking forward to our next visit!
Guest favourite
Cottage in Cape Charles
4.8 out of 5 average rating, 111 reviews

Sea Salt Cottage: Tranquil Getaway 5 min to beach

NicoleRating, 5 stars1 week ago
This was the perfect find for exactly what we needed- a peaceful and quiet few days to escape our hectic everyday. The home was cozy and lovely and exactly as described. Cape Charles is a gem of a town and we look forward to coming back!
Guest favourite
Cottage in Gloucester Courthouse
4.98 out of 5 average rating, 211 reviews

Historic Ware River Cottage at Glebefield

LisaRating, 5 stars2 weeks ago
What a wonderfully charming and peaceful cottage, and it was absolutely perfect for a quiet getaway. Having Nuttall’s Store just a short drive away was so convenient for necessities, and their steaks and sandwiches are amazing! Thanks for everything ☺️
Guest favourite
Cottage in Middleburg
4.95 out of 5 average rating, 197 reviews

Waterfront Cottage at Goose Creek

Jane BRating, 5 stars2 weeks ago
What a wonderful, peaceful, relaxing home! This is one of the nicest places were we have stayed. The cottage is spotless and comfortable. The location is ideal, minutes from the center of town, yet totally private overlooking Goose Creek. We even had three deer visit us two of our mornings. We will definitely stay here again on our next visit to the area.

Private cottage rentals

Top Guest favourite
Cottage in Colonial Beach
4.93 out of 5 average rating, 262 reviews

Cozy cottage 3 blocks from beach

PujaRating, 5 stars1 week ago
Me and my boyfriend wanted to find a place to get away and this was a great spot to feel especially near the wonderful beach & setting, We love their backyard and creative decoration in the cottage!
Top Guest favourite
Cottage in Norfolk
4.98 out of 5 average rating, 248 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

DawnRating, 5 stars1 week ago
We stayed at Richard’s because we were getting married on the beach which is right behind the house however weather halted tht so we opted to get married right in his beautiful backyard. The first day we were there we met his father who introduced himself and let us know tht if there was anything we needed to just reach out. Richard and his Mom actually were very sweet and left us a beautiful card for our wedding, the house is gorgeous and it was very clean. There were a lot a personal touches in the house tht made it truly feel like you were home. I can’t wait to stay there again next year for our 1st year wedding anniversary.
Top Guest favourite
Cottage in Greenbush
4.98 out of 5 average rating, 127 reviews

Bell Farm Cottage LLC - quiet and peaceful

SharonRating, 5 stars5 days ago
So glad we chose Bell Farm Cottage for our girl's mini get away! Perfect place and location for our needs. We will definitely be back.
Top Guest favourite
Cottage in Smith Island
4.97 out of 5 average rating, 223 reviews

Levering Creek Cottage with Private Dock

LindsayRating, 5 stars1 week ago
We loved our stay at Janet’s place! She was incredibly easy to communicate with, and the house was absolutely perfect—comfortable, clean, and well-appointed. We especially enjoyed being nestled into Ewell, with convenient access to the water, shops, food, and golf cart rentals. It made for a truly relaxing and memorable getaway.
Guest favourite
Cottage in North East
5 out of 5 average rating, 33 reviews

Vintage Waterfront Cottage with Stunning Sunsets

AmandaRating, 5 stars4 months ago
This was our second stay at this cozy cottage, and it was just as wonderful as the first! Every detail is thoughtfully considered, from the clean, stylish interiors to the warm ambiance. The indoor fireplace and outdoor fire pit (perfect for s’mores under the stars) were highlights, and the bay views from the viewing platform never disappoint. Sue & Mark are incredibly friendly and communicative, always quick to help with anything we needed. We also appreciated the provided firewood and all the little extras that made the space feel so comfortable and welcoming. Thank you for another amazing stay – we can’t wait to return!
Top Guest favourite
Cottage in East New Market
4.95 out of 5 average rating, 63 reviews

Cottage on Cabin Creek

MicheleRating, 5 stars2 days ago
It was a great stay. Host was responsive and home was calm and clean. Loved seeing the osprey from bed! Those windows highlighted the beautiful view. The weather was a bit dumpy but the space provided everything we needed.
Guest favourite
Cottage in Sussex County
4.97 out of 5 average rating, 120 reviews

Private Cottage * 1 bedroom+loft * Rehoboth Beach

SharonRating, 5 stars2 weeks ago
Cleopatra's place was cozy and clean, except for the pollen on the screened in porch, which I learned is typical during the spring off-season time when we visited (in mid-April). Cleopatra is very responsive and the place and looked just like the photos. The house is nicely situated away from the hustle and bustle of the boardwalk and surrounding area, but still within walking distance to the beach and town. It was lovely to come back for a break away from the crowds, and to prepare some simple meals in the well-equipped kitchen. We discovered a nice walking trail on the last day, which is also possible to cycle on, and only wished we knew about it before! My only complaint is that the bicycles were in disrepair. Though functional, they need some maintenance and repairs. But they might already be upgraded for the next guests given how responsive Cleopatra is! We still managed to explore and enjoy the area. Highly recommend walking near the lake as well as the beach!
Superhost
Cottage in Chincoteague
4.76 out of 5 average rating, 17 reviews

Holiday Cottages-Nautical Cottage

DavidRating, 5 stars3 weeks ago
Flawless from start to finish. I've stayed in dozens of high-end hotels across the country, and this little cottage was THE cleanest space I've ever had the pleasure of staying in. Everything glistened like it was new. My family and I felt very much at home from the time we entered to the time we left. Top notch! Many thanks for a job well done and facilities that didn't disappoint.

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