
Chesapeake vacation rentals
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Top-rated vacation rentals in Chesapeake
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Vacation rentals for every style
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Popular amenities for Chesapeake vacation rentals
Vacation rentals with jacuzzis in Chesapeake

Kingsgate 2 Bedroom (7-Day Minimum Special)
My family and I had a wonderful stay, we loved the king size beds and had an overall great time. We liked the privacy and considering the reason for our stay it was a perfect match for us.

Kingsgate Resort, Williamsburg, VA-Sleeps 4
Cynthiaās place was AMAZING! The place was spotless and we felt at home as soon as we walked in. Check in was so easy and Cynthia was always available to answer any questions that we had. Would 10/10 recommend staying with Cynthia. We will definitely be returning! š

Greensprings Resort- 4 bedrooms sleeps 12
Scott was a stellar host. Easy, clear, and concise instructions and was readily available for all questions and concerns. wouldn't hesitate to contact for future bookings.

Baybreeze @ Buckroe -hot tub, sauna, game rm. 5bd
Rachelās place was one of the reasons why our spring break was so amazing this year. As soon as you enter the house you notice the cozy beach vibe theme. The house is nicely organized and put together. The game room was a fun addition as well. The backyard is well kept with the beautiful green grass cut and edged. The gazebo area has a fire pit and hot tub. Let me tell you⦠such an amazing vibe in the back yard. We had so much fun listening to music and making smores all night! They thought of everything here! Thereās an actual sauna in the master bedroom. I was bummed because we forgot our wireless speaker at home, but guess what⦠they have one available for you to use and fully charged! Letās talk about the furniture. They actually put money into the furniture here. The couch was huge and cozy. The beds were not stiff at all. In fact my kids bragged about how comfortable their bed was and how they couldnāt wait to hit the hay that night! This place is worth every penny.

Wyndham Governor's Green (3 BD Deluxe)
Great location, private and peaceful. Staff was very helpful and friendly.

Hot Tub - Massage Chair - Golf Cart - Beach Gear
The house and the host were incredible. Immediately upon arriving, we felt at home and ready to relax. There are so many five star touches in this house --- every room has its own sound machine; there is a top notch massage chair in the living room; and there is ample space to get away while all being in the same home. Our kids were asking within the first hour if this could be the forever house. I am looking forward to booking this space again in the future!

Patriots Place 2 Bedroom Lockoff
Great place to stay! Would definitely recommend and stay there again. It is located close to shopping and dining as well as Busch Gardens and other attractions.

Spring Hill Guest Cottage - Portsmouth
Susan and Ron were delightful, hospitable, and their kindness was indescribable. They were welcoming and made me feel at home. The cottage was everything they said it was. Checkin was easy and the cottage was clean and cozy. The provisions were above and beyond. The pool area and fire pit was extremely relaxing. This stay was great not only for the cottage but for the great hosts and Barkley. ššš©µā¤ļø I can't wait to stay here again. Thank you, Susan and Ron.
House rentals in Chesapeake

Lakeside Oasis - Walk 2 everything! 3Blocks2Beach
We cannot thank Star & Austin enough for opening up their beautiful home! Very easy to find, close to restaurants, activities and the beach. The home was immaculate. We will stay here again in the future.

3 bedroom private home a block from the beach!
Kateās place was perfect for our familyās first trip to Norfolk! The beach is literally less than a 5 minute walk away. Her home is adorable and her neighbors are the sweetest people! My kids loved their little dog. We felt very comfortable in the house ā very nice neighborhood and the home had everything we needed! We were very close to downtown as well. We will definitely be coming back if we make it back to Norfolk! Thank you Kate!

3 bedroom home minutes from Buckroe Beach
Had a great time staying at Lisa's home. The place was a very beautiful home and a peaceful neighborhood. Spacious living area as well as the bathrooms and rooms.

Lakefront House @ Oceanfront
Responsive even before I booked. As pictured. Accommodated 5 of us very comfortably. Friends stayed one half block up I liked our place much better!

Cozy Country Cottage
Nice quite location

Charming house close to beach and shops!
Heron House was perfect! Great location to walk to the beach and to Mason Street shops. Our party of four was completely satisfied with the layout of the house and the many amenities. We will stay here again!

Play by the Bay 1 MIN TO WATER
We had a wonderful stay at Dianaās Airbnb off Shore Drive on Denwiddie From the moment we walked in, we could tell how much thought and care went into this place. The attention to detail was incredibleāfrom the beautifully curated dĆ©cor to the small but thoughtful touches like Band-Aids, cooking essentials, and other convenient extras that made a big difference. The location was perfect, and the space truly felt like home. Thank you, Diana, for creating such a welcoming and comfortable space!

Chesapeake Bay Beach house (Chicās Beach) 1 block!
This place was perfect for the kids and parents and grandparents. We enjoyed our stay here walking distance to the beach was perfection. It was so peaceful, clean and spacious. We enjoyed the downstairs yard & patio area. We didnāt get to use the bbq grill but next time we stay here we will. Beautiful home. Thank you
House rentals with jacuzzis in Chesapeake

Wooded Wonderland Miniature Golf Hot tub Pool
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!

1-Bedroom Home Near Christopher Newport University
We were in town to visit family nearby and the location was perfect. We did not spend much time at the house but in the evening had a chance to try out the hot tub, which was wonderful, and everything was clean. If you hear music out of nowhere, there is a clock that chimes a song- it is not the ice cream man or Alexa going rogue lol. Adam was helpful ahead of the trip and responsive. He left very thorough instructions and recommendations for us. There were lots of pillows for the bed and we found the mattress comfortable (I was nervous from a few reviews about it being too firm). Frankie was often hanging near the entrances and front bushes, so just be mindful when opening the doors that she may want to sneak in. Overall, great stay!

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
Incredible views of the water. Sunrise is beautiful. Dolphins swim by. Hot tub and fire pit are fabulous. Our hosts were extremely responsive and helpful, friendly, and proactive. Our family had a great time at their home.

Coral Cove- Backyard-Hot Tub-Walk to beach-Dogs ok
This was the perfect place for our family of 4 to stay. The host was very kind and helpful with instructions. The space was clean, comfortable, and had everything we needed. We were impressed by the accommodations that were included for small children (pack-n-play, high chair, etc)! We would definitely stay here again.

Splash of Lime Carova 4x4 Beach Cottage
Martinās place was BEAUTIFUL and SO clean! Very roomy and beautifully decorated with all the amazing attention to details! The wild horses that came to visit the property were so beautiful and fascinating to watch! I will absolutely be back and 1000% recommend Martinās place! Martin was also an incredible host with his attentiveness and even talked me through driving on the beach since it was my very first time ever driving on sand⦠I was terrified lol But he was able to calm me down via the phone and I got there safe and sound with no issues! Awesome stay!! š

Bright 5BR3.5BA Sleeps 12 Hot tub Close to Beach
We had a great stay! Laura was super responsive when we had questions and everything was easy. House was well-equipped overall, especially the kitchen and outdoor shed. It was so nice to have sheets and towels waiting for us. The kids loved the decks and swings outside and the play area on the landing. It was lovely having the community pool right across the street and the community beach access with bathrooms close by. We took a morning to walk to the nature preserve and an afternoon at the lighthouse. Lots of great memories were had. Thanks so much for sharing your home with us for the week!

7 Bedroom | Corolla Light Resort | Private Pool &
Lily Beth was the PERFECT place for our family Thanksgiving adventure. First Andrea(the host) was amazing when we were trying to book. We didn't book until about a month out. She was very quick to respond to any questions we had. She was also willing to accommodate a couple special request we had. When we travel one of the most important things to me is that the place we are staying is clean. This house definitely was that. I had zero issues with my children, one who is crawling, being on the floor playing. Every part of the house was clean. The kitchen is great for large groups with lots of cooks. Plenty of space for all to cook and prep at the same time. The kitchen is VERY well stocked. The location was awesome. The sound is right outside and the beach is a short few blocks away. We would definitely return to this house to stay again in the future. I would say the only downside is that I wish there would have been 2 refrigerators in the house.

Island Lotus Yoga & Spa
Stop searching for a place and book this one. Right now. If you're looking for a tranquil oasis to get away from it all, this is the property for you. The house itself was relaxing and spectacular. I never wanted to leave the sunroom! Yoga with Mari was so much fun and we even got to visit baby goats on the farm with Kristen. The only warning I have is- be prepared to never want to leave. I'm already excited to return! There were fresh eggs left for us, as well as freshly baked blueberry bread. The soap from the goat farm was divine! Be sure to spend plenty of time in the hot tub and get out and look at all of the stars. Nature is truly beautiful in this place. If I could give it ten stars, I would. Thank you, Quang and Mari for such an incredible stay!
Quick stats about vacation rentals in Chesapeake
Total rentals
970 properties
Total number of reviews
32K reviews
Family-friendly rentals
440 properties are a good fit for families
Pet-friendly rentals
280 properties allow pets
Rentals with a pool
130 properties have a pool
Rentals with dedicated workspaces
510 properties have a dedicated workspace
Frequently Asked Questions
Where should I stay in Chesapeake?
Make yourself at home in Chesapeake by choosing from our most frequently booked neighborhoods. We have over 500 vacation rentals in Olde Towne, over 500 vacation rentals in Downtown Norfolk, over 270 vacation rentals in Ghent, and over 110 vacation rentals in Salem.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 510 vacation rentals in Chesapeake featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesapeake?
Four-legged friends are welcome in Chesapeake. Choose from more than 280 vacation rentals for guests traveling with pets.
Are there Chesapeake vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 130 vacation homes with pools in Chesapeake, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Chesapeake?
Experience the best of Chesapeake with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesapeake have a bbq area?
Absolutely! We offer over 110 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Chesapeake have a gym?
Absolutely! We offer over 10 townhouse rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chesapeake have self check-in?
Absolutely! We offer over 40 apartment rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Chesapeake?
Chesapeake has more than 440 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Chesapeake?
Enhance your stay in our House Rentals with the most popular amenities: over 130 homes with self check-in, over 60 homes with a gym, over 110 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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