
House holiday rentals in Chesapeake
Find and book unique houses on Airbnb
Top-rated house rentals in Chesapeake
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Chesapeake
House rentals with a pool

York River Vacation Home
We had a wonderful stay here! Everything was exactly as described. Eugene was really responsive when communicating and super friendly! I would highly recommend staying here if you get the chance. Thank you again for such a relaxing place to stay!

Elegance Escape on Saunders Dr
My family and I absolutely love our "Home away from home." This was our 2nd year enjoying all of the elegance and fun your home has to offer. Giovanni and family are the best host's that we have ever had. Communication is so important, and any time I reached out, I was quickly responded to. We got into town a little early, and they were very accommodating when they didn't have to be. The home is immaculate and warm and we didn't have to leave to be entertained. Visiting my son, who is active duty military is even more amazing when you have such a beautiful home with plenty of family things to do right at your fingertips. The neighborhood is peaceful and we felt safe and secure in our own private oasis! Thanks so much for making our stay just as amazing as the 1st time. Looking forward to our next trip!!

Gorgeous Vacation House
The house was super clean when we got there, the temperature of the house was great the entire stay. The pool was certainly clean, but since we went early, June the water was a little bit cold, but it felt really nice and refreshing honestly. There were three beach chairs and a wagon there that were helpful for traveling to the beach. There were available cups plate, utensils, and all the necessities that you would need, they even had shampoo and conditioner bottles there for us. We weren’t aware that there was a code to get into the house so instructions for check-in were a little bit unclear, but all I had to do is message and they responded. Overall, I would recommend staying here because even though the area surrounding isn’t the nicest, I felt safe the entire time at that house!

Stunning Views of Back Bay & Seconds to the Beach
Great location and host. The home was the perfect size for my family and friends.

Perfect Getaway!
We had a great family visit at this house. We really enjoyed the pool and whole house was very comfortable and clean! It was nice to just hang all day by the pool or top for a sanctuary from a long day of events. Sabrina was very attentive and responsive with questions and situations, appreciate her flexibility as a host!

Sunrise, North End Beach
The best spot. Super nice amenities and very clean, great location, right across the street from beach access.

Beach Home, Upscale Croatan Resort + Private Pool
Such a wonderful place!! Beverly was more than accommodating and was very responsive to all of our questions🙌🏽 we would love to stay here again in the future

Casita View Get Away
Had a great stay.
Weekly house rentals

The "Bison" contemporary retreat (King Bed)+
The place was beautiful inside and out. My family and I felt like we’re at home. I love the outdoor space. Most of the times, my parents and I chilled outside enjoying the weather and chitchatting with each other. My family and I came down from Pennsylvania to visit my sisters who live about 10-15 mins away from the home. My family and I had a great time during our weekend stay. Hopefully one day we’ll come back and stay at this beautiful home again. I highly recommend this beautiful home. Definitely 5 stars :)

Beautiful home in Chesapeake
⭐️⭐️⭐️⭐️⭐️ We had a wonderful stay! The location was perfect—close to everything we needed and in a neighborhood that had such a nostalgic, charming feel to it. The home itself was spotless and well cared for, and Keyonna was incredibly friendly and welcoming, which made the experience even better. It truly felt like a home away from home. We’d definitely stay here again!

The Bartlett Inn
Stayed here was a family event it was spacious with a well equipped kitchen . The neighborhood was very quiet and safe could walk for miles without seeing a car or busy street .

Convenient Location!
We have just returned home from Deborah’s place and let me just say, after arriving and walking through the home I could feel the warmth and love poured into this home. It was welcoming and peaceful and awww, before long we were home. Deborah thought of everything to ensure the home is comfortable. This home literally has everything we needed for our entire stay. Such a nice touch! The kitchen had everything, and everything worked flawlessly. Deborah, your attention to detail is a gift! My family and I thoroughly enjoyed your home, and are definitely look forward to returning when next we visit Va Beach. Thank you for opening up your childhood home to us. We thought of your family as we moved around the home. See you soon!

Home Away From Home
Place was as described and all info was given and easy to understand definitely worth staying if your in that area

Home away from Home.
Far enough away from the busiest sections but close enough to get to where we needed in a short amount of time. Only one suggestion....maybe some lamps in the bedrooms. It was SUPER clean and Criska was AMAZING

Backyard Bungalow | Near Beach
Awesome hosts, great communication and very nice home

Historic Haven
Amazing place would totally come back to stay again.
Private house rentals

Private Beachfront Modern Villa: Outdoor Shower!
This was our second stay at this Airbnb and we were incredibly glad we decided to book again! The place is exactly as described, has all the beach supplies so you don’t need to pack it all, is just a quick walk to beach (awesome with kids), and the view can’t be beat. Heidi was an extremely responsive host who went above and beyond to make sure our stay was fantastic - you can tell her priority is the guest! My family of 5 plus a grandma enjoyed lazy mornings on the patio, taking in stunning sunsets over dinner, and long days on the beach (bathroom breaks back at the house are a snap due to the close proximity). The outdoor shower with warm water is especially helpful with kids! We will be back at least twice this upcoming year. Thanks for another great stay!

941 Coastal Luxury Retreat
It was a great place to stay! Super clean and comfortable. Many great places with if walking distances or a short drive. The farmer’s market is a must do! Carrie was super helpful with a question during the stay. We would stay again!

Tudor Treasure in Olde Towne
We had a wonderful stay at Karen’s home! The space is full of charm and personality, with beautiful decor throughout. Karen went above and beyond—she left a thoughtful note, local recommendations, snacks, light breakfast options, and lots of coffee choices with creamer. The outdoor space was peaceful and relaxing, and the neighborhood is perfect for walking and exploring the historic town. Some suggestions: -Fish & Slips – A scenic walk, great food, and happy hour. -The Bier Garden – Family-owned, excellent food, and a beautiful garden. -The Coffee Shoppe – Great coffee, breakfast, and lunch. Highly recommend taking the ferry into Norfolk for the day. We’re so glad we spent a weekend in Portsmouth and have already recommended the trip to others!

Paint The Beach Pink! Full House | Private Pool
Check in was super easy, the AC was on when we arrived which was great after a long Uber. The pool felt nice and the whole backyard area was fantastic. We ended up using the bikes a lot more than we thought which was a lot of fun. It's a quick bike ride to the boardwalk and walking didn't take too much longer. Bradley was very quick to respond whenever I had a question about anything. If we come back to Virginia Beach we will definitely be checking the availability of this house!

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!
This home stands out among the many air B&B’s I have stayed it. Emily and Abel provided many extras such as cold water and snacks when we arrived, beach towels for our use, dog food bowls for our dog, soft beds with plush throws to use at our leisure. The neighborhood is walkable filled with southern charm. Our family used this home as a gathering place for my son’s wedding. It exceeded my expectations.

Seize the Bay
What a wonderful job our hosts did! They provided all the supplies we could possibly need and then some! They truly thought of everything. We only had to buy food for ourselves, while most air bnb’s we’ve stayed in have one roll of toilet paper, one roll of paper towels, one trash bag, a tiny bottle of dish soap, etc. It felt more like staying at a friend’s home than a stranger’s. It was very short walk to the beach, which was very convenient. The beds were incredibly comfortable and having a recent back injury, this made a huge difference for me. They provided clear instructions about everything, we never had a need to contact them, though I’m sure they would’ve been very responsive if we had. I don’t have any complaints or suggestions for improvement at all!

Modern retreat
Where do I begin Tam’a place was very nice the pictures don’t give it enough credit .This house will have everything you need. She was quick to respond and will help with what ever you need , everything was great! I definitely will be returning when ever come to EC visit family again . Thanks again 🥰🥰

Riverfront Home w/ Vintage Vibes
Sarah’s Portsmouth home exceeded our expectations. Coming from Phoenix, we were looking for a peaceful, welcoming place to unwind with family and this home delivered. It was clean, cozy, and full of charm. Mornings were especially memorable with coffee on the deck while birdwatching and enjoying the quiet surroundings. We didn’t feel the need to plan activities — simply being together in such a relaxing space was more than enough. It felt like a true retreat. Thank you, Sarah, for sharing your beautiful home!
Quick stats about house rentals in Chesapeake
Total rentals
560 properties
Total number of reviews
13K reviews
Family-friendly rentals
280 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
310 properties have a dedicated workspace
Destinations to explore
- Virginia Beach Holiday rentals
- Williamsburg Holiday rentals
- Richmond Holiday rentals
- Shanghai Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- Beachfront rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with lake access Chesapeake
- Apartment rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with breakfast Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with outdoor seating Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a firepit Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Cottage rentals Chesapeake
- Beach house rentals Chesapeake
- Family-friendly rentals Chesapeake
- Waterfront rentals Chesapeake
- Flat rentals Chesapeake
- House rentals Virginia
- House rentals 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
- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
- Water Country USA
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Currituck Beach Lighthouse
- Outlook Beach
- Jamestown Settlement
- Haven Beach
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Kiptopeke Beach
- Golden Horseshoe Golf Club