
Chesapeake Beach beach vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chesapeake Beach
Guests agree: these vacation rentals 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 Beach vacation rentals
Stay near Chesapeake Beach's top sights
Vacation rentals in Chesapeake Beach

The Glebe
Excellent stay at RivahLife! The views were spectacular and the home was exactly as described. Easy to find with lots of stuff for the kids and adults. Looking forward to returning during the warmer months as the fishing, boating, and swimming would be more desirable. Thanks for the high chair and portable crib. Those things really help when traveling with kids.

Patterson Park Apt; Walk to Hopkins, Bars, Cafes
Jenny’s place was exactly what we needed for our long weekend trip. I loved that it was spacious, clean and had excellent natural light. We spent lots of time walking through the park across the street and appreciated how quiet the street/block was at night. 10/10 would recommend!

Crow’s Nest Cottage - Down Under: Chesapeake Bay
I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

Rockfish Keeper
The house was exactly as described and it was so easy to communicate with them as they responded to texts within minutes

2-bedroom lake-house with a magnificent view
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!!!

Relax by the Water - Summer Dates Available!
Absolutely beautiful home! highly recommend!

Waterfront getaway Essex, MD
A great place to spend time with the family with incredible views

1943 Beach House Walk to Town & Beach & Boardwalk.
I was in town for work, and this place was perfect. It was walkable to several restaurants and to the calming water. Christopher was a wonderful host and very responsive. I'd definitely stay again if in town.
Other great vacation rentals in Chesapeake Beach

House in Edgewater Maryland
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.

Family Ready Dogs OK Ping Pong Backyard EV Charger
Absolutely gorgeous home. ALL the amenities! Master bedroom is HUGE. Master shower is superb!! All bedrooms are nice sized and all have their own bathroom. Basement is really nice too. Can’t say enough good about this home. Would definitely rent again!!

⇚Family Getaway⇛| Lakeside + A Nature View |
Kevin is a great host to us year after year! we love staying at his place!

Beautiful Home Near Beach and Patapsco River
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.

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms
Excellent host! Great communicator and went out of her to make sure we didn't have any issues. Lovely place for a family get away!

Entire family size house steps to ANC & metro walk
Tyler's place was perfect for our stay with our extended family. It's spacious and comfortable, with plenty of room to relax indoors and out. It has a very nice large porch and deck, great for some solitude or for kids to play. The beds were comfy and the linens ample, there are gorgeous large bathrooms and luxurious showers, the kitchen was well-stocked and included an amazing high-end stove, and the living spaces are nicely decorated and furnished with art and tons of books. One bedroom had lots of toys and kids' books, a very nice touch. Tyler was helpful, accommodating, and responsive. The location is very convenient to Arlington National Cemetery and within walking distance to a Metro stop. Everything about this rental was fantastic--we highly recommend it if you need a lovely space for a large group. Thanks, Tyler!

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

Garden Getaway
We had the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!
Destinations to explore
- Washington Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- Pocono Mountains Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Plainview Vacation rentals
- Outer Banks Vacation rentals
- Long Island Vacation rentals
- Hudson Valley Vacation rentals
- The Hamptons Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Nationals Park
- The White House
- Lincoln Park
- National Mall
- Hampden
- National Museum of African American History and Culture
- Georgetown University
- Sandy Point State Park
- Smithsonian American Art Museum
- Smithsonian National Museum of Natural History
- Arlington National Cemetery
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- Washington Monument
- National Harbor
- Great Falls Park
- Oriole Park at Camden Yards
- District Wharf
- Six Flags America
- American African Museum
- Meridian Hill Park
- Congressional Country Club
- M&T Bank Stadium
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes