Holiday houses in Chesapeake Beach

Find and book unique accommodation on Airbnb

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Popular amenities for Chesapeake Beach holiday rentals

Stay near Chesapeake Beach's top sights

Chesapeake Beach Water Park16 locals recommend
Hook & Vine - Kitchen and Bar18 locals recommend
Neptune's Seafood Pub9 locals recommend
Sweet Sues Bake Shop & Coffee14 locals recommend
Chesapeake's Bounty3 locals recommend
North Beach Farmers' Market3 locals recommend

Other great holiday rentals in Chesapeake Beach

Guest favourite
Home in Edgewater
4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

NancyRating, 5 stars3 weeks ago
Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.
Superhost
Home in Pasadena
4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

EvaRating, 5 stars1 month ago
This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.
Guest favourite
Cottage in Colonial Beach
4.86 out of 5 average rating, 88 reviews

Bungalow Private Beach & Dock Colonial Beach Water

CristaRating, 5 stars3 months ago
Quiet and cozy home in the perfect location. We had a wonderful stay with beautiful views of the water (too cold in Feb to fully enjoy), and it was so convenient to be able to walk to local coffee shops and restaurants. Would definitely stay here again!
Superhost
Home in Montross
4.88 out of 5 average rating, 232 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

SarahRating, 5 stars2 weeks ago
This cabin was everything we wanted and more! It’s in the perfect location, just a short drive to so many activities but also tucked away offering privacy. The house was so cozy it put us at ease as soon as we walked in. The owner was proactive and very quick to respond, including sending a great packing and local activity list a couple days in advance of our trip which came in very handy. Activities: This rental comes with guest passes to the private Shark Tooth Beach where our kids had so much fun finding real shark and manta ray teeth in the sand! Westmorland State Park and George Washington’s Birthplace both had great hiking and beaches for the kids. We visited Garners Produce twice where the kids fed animals and pedaled toy tractor’s while we picked up farm fresh milk and eggs. We spent our afternoons kayaking on the quiet lake soaking up the sunshine. We will definitely book another vacation at this cabin. You will not be disappointed with your stay at this little gem!
Superhost
Cabin in Lusby
4.84 out of 5 average rating, 171 reviews

2-bedroom lake-house with a magnificent view

MohamedRating, 5 stars2 weeks ago
Beautiful house and beautiful view. Outdoor jacuzzi with the view is not to be missed! Gorgeous and clean home. The private site made it an amazing getaway from busy life. Thank you, we will be back soon!!!
Guest favourite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars3 months ago
I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.
Superhost
Home in Manassas
4.77 out of 5 average rating, 13 reviews

Luxury Home. Hot-tub, Fire Pit, Game Room. IAD/DC

AaronRating, 5 stars3 weeks ago
Very fun place! Perhaps somewhat new so some kinks being worked out, but the host is incredibly responsive to any requests and has invested heavily in the property - luxury fixtures, appliances, amenities. Highly recommend.
Superhost
Farm stay in Queenstown
4.75 out of 5 average rating, 16 reviews

⤛Windy Hill Farm Retreat⤜ |Private+Destinational|

DanielRating, 5 stars21 months ago
Kevin was a great communicator with me for our weekend with friends and made sure we had everything we needed. If you care to leave, his place is located a close drive to lots of fun activities like kayaking in the bay and eating crabs.

Destinations to explore