Cottage vacation rentals in Chesapeake Bay

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Popular amenities for Chesapeake Bay cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Harpers Ferry
4.85 out of 5 average rating, 184 reviews

Wild & Cozy | Harpers Ferry Mountain Escape

KevinRating, 5 stars1 week ago
Good quiet place to stay near Harper’s Ferry. Place was clean, hot tub was nice we were able to watch deer next door and across the street hang out and graze. Everything was in place and clean. Beds were soft and comfortable. The only issue that I have is the rocks that line the driveway especially when turning out of the driveway will catch lower vehicles and cars it caused a little damage to my wife’s car and be careful where you park there is an oak tree with dead and rotting limbs that need to be trimmed that are right above the area where cars would park if you have more than one car. If I were to ever come back to Harper’s Ferry I would definitely stay there again.
Guest favorite
Cottage in Saint Leonard
4.96 out of 5 average rating, 136 reviews

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

AuroraRating, 5 stars2 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 favorite
Cottage in Lower Township
5 out of 5 average rating, 217 reviews

Octopus Cottage: Hot Tub | Kayaks | Fire Pit

MonicaRating, 5 stars1 week ago
Do not hesitate to stay here! It is spectacular. Right on the beach, immaculate and perfectly appointed. We can’t wait to come back!
Guest favorite
Cottage in Hamilton
4.95 out of 5 average rating, 372 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

CalvinRating, 5 stars2 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 favorite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 167 reviews

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

MikeRating, 5 stars3 days 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 favorite
Cottage in Harpers Ferry
4.97 out of 5 average rating, 101 reviews

Peaceful Lakefront Cottage with Mountain Views!

SusanRating, 5 stars2 weeks ago
We loved staying at the lakefront property. The weather didn't allow us to spend much time in the amazing outdoor spaces at the home, so we will be back in warmee weather. The house was so comfortable and the view was amazing. We had everything we needed for a cozy mountain weekend away. We will definitely be back!
Guest favorite
Cottage in Harpers Ferry
4.92 out of 5 average rating, 173 reviews

Family & Pet Friendly- Hot Tub-Full Kitchen

WilliamRating, 5 stars2 days ago
Had a great stay, the house is a great place to bring family or friends
Guest favorite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 175 reviews

*The Artist's* Hot Tub- Fire Pit-Private Back Yard

MatthewRating, 5 stars1 week 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 favorite
Cottage in Wildwood Crest
4.91 out of 5 average rating, 185 reviews

Cozy Cottage 1.5 Blocks from Beach; Pet Friendly!

TomRating, 5 stars2 days ago
We had a great time. Couldn’t be happier with the Airbnb.
Guest favorite
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 favorite
Cottage in Lewes
4.87 out of 5 average rating, 201 reviews

BnB’s Dog-Friendly Cottage

SydneyRating, 5 stars1 week 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 favorite
Cottage in Cape May
4.9 out of 5 average rating, 247 reviews

House on the Hill- Dog Friendly Near Cape May

SandraRating, 5 stars1 month ago
A lovely charming dog friendly home. It was a short drive to beaches, shops and restaurants. Ellen and Michael are wonderful hosts. The dogs enjoyed resting on the back porch and playing in the fenced in yard. We could not have asked for a more comfortable place for our stay in Cape May. An absolute gem.
Top guest favorite
Cottage in Norfolk
4.97 out of 5 average rating, 325 reviews

Lovely Ocean View Cottage

ShellyRating, 5 stars1 week ago
Very peaceful and fenced in yard was a plus for our small dog. The beach was only a couple of blocks away. House was clean and host was responsive.
Guest favorite
Cottage in Cape Charles
4.8 out of 5 average rating, 110 reviews

Sea Salt Cottage: Tranquil Getaway 5 min to beach

MicheleRating, 5 stars1 week ago
This was an amazing Air BnB find ! The house was very clean and comfortable. It was close to everything, including the local brewery, beach, restaurants and shopping. There was nothing lacking in this rental. We traveled with two small dogs and they loved it too. Thank you for sharing your beautiful home! We would definitely come back!
Guest favorite
Cottage in Middleburg
4.95 out of 5 average rating, 196 reviews

Waterfront Cottage at Goose Creek

RandolphRating, 5 stars2 weeks ago
Secluded location, nice, quiet and peaceful. There is one house next door but didn’t see or hear anyone the entire time. The property is surrounded by woods and a large creek down below out the back. I have a real Service Dog, Malinois/Lab mix who is also off leash trained and I was able to let her enjoy being a dog for a while roaming the property and woods. The only negative is the lack of window coverings in the bedroom/bath room. To compensate we left the outside lights on at night which worked well to allay our fears. The house was very clean and all of the appliances are quite new and worked very well. The house heater is excellent, the shower has water pressure and hot water for days! The internet and TV worked extremely well and there is good cell phone signal. The road is gravel so a very low clearance sports car might have trouble so don’t bring your Corvette!! The house is less than 10 minutes to downtown Middleburg and has a small Safeway. All in all a great experience.
Top guest favorite
Cottage in Powhatan
4.94 out of 5 average rating, 270 reviews

$75 (Sun-Thur 1 nights) $125 (Fri-Sat) Pets.

KianaRating, 5 stars1 month ago
Such a cute place to stay! Everything was well maintained and we felt very safe. The animals are all adorable. Would highly recommend

Private cottage rentals

Top guest favorite
Cottage in Colonial Beach
4.93 out of 5 average rating, 261 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 favorite
Cottage in Norfolk
4.98 out of 5 average rating, 247 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

DawnRating, 5 stars2 days 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.
Guest favorite
Cottage in Deale
4.96 out of 5 average rating, 158 reviews

Chesapeake Bay Cottage

AndyRating, 5 stars2 weeks ago
fantastic stay. clean and very quiet right on the bay. highly recommended. would definitely revisit again.
Top guest favorite
Cottage in Greenbush
4.98 out of 5 average rating, 125 reviews

Bell Farm Cottage LLC - quiet and peaceful

CharlesRating, 5 stars3 days ago
My wife and I needed a short getaway and Tia's place fit the bill. It is just as it looks in the photos - spotless and cozy. Tia is a great host and a nice person as well; she showed us her hens and chickens that are nearby and she is also a beekeeper. The house is comfortable and we felt right at home. It's only a short drive to many restaurants and antique shops; we will definitely be back when we need a little time away. Highly recommend.
Top guest favorite
Cottage in Smith Island
4.97 out of 5 average rating, 222 reviews

Levering Creek Cottage with Private Dock

LindsayRating, 5 stars2 days 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.
Top guest favorite
Cottage in East New Market
4.95 out of 5 average rating, 62 reviews

Cottage on Cabin Creek

JenniferRating, 5 stars3 weeks ago
We would highly recommend this peaceful and relaxing cottage. We especially loved the views, the dock for fishing, & the views from the bedroom. Janelle was very helpful with places to visit as well as working out an issue that came up at the property. She was quick to respond & made every effort to make sure we were comfortable. Would definitely stay here again! 😊
Guest favorite
Cottage in Sussex County
4.97 out of 5 average rating, 120 reviews

Private Cottage * 1 bedroom+loft * Rehoboth Beach

SharonRating, 5 stars1 week 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 stars2 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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