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Chesapeake vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Chesapeake vacation rentals

Stay near Chesapeake's top sights

Waterside46 locals recommend
Chrysler Museum of Art56 locals recommend
Nauticus78 locals recommend
MacArthur Center20 locals recommend
Waterside District54 locals recommend
Topgolf41 locals recommend

Vacation rentals with jacuzzis in Chesapeake

Superhost
A well-equipped kitchen features dark wooden cabinets and light granite countertops. An oven, microwave, and refrigerator are present, alongside a sink and countertop appliances. A knife set is organized on the countertop, and essential kitchen items are neatly arranged for convenience.
Apartment in Williamsburg
4.88 out of 5 average rating, 8 reviews

Kingsgate 2 Bedroom (7-Day Minimum Special)

ChloeRating, 5 stars5 months ago
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.
Superhost
Aerial view showcases a resort-style area featuring a large swimming pool surrounded by lounge chairs. Well-maintained mini-golf courses are visible alongside a tennis court, all framed by lush greenery and neatly arranged landscaping.
Apartment in Williamsburg
4.6 out of 5 average rating, 10 reviews

Kingsgate Resort, Williamsburg, VA-Sleeps 4

JackieRating, 5 stars22 months ago
Cynthia’s 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! 😊
Superhost
The resort building features a harmonious blend of brick and siding, showcasing large windows and a welcoming entrance. Lush greenery and manicured landscaping enhance the exterior, complemented by a clear blue sky above.
Apartment in Williamsburg
4.95 out of 5 average rating, 39 reviews

Greensprings Resort- 4 bedrooms sleeps 12

BenjaminRating, 5 stars8 months ago
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.
Superhost
A hot tub is enclosed within a shaded gazebo, illuminated by soft lights. The surrounding fence adds privacy, while the serene blue water invites relaxation. The evening setting creates a calming atmosphere, perfect for unwinding after a day of activities.
Home in Buckroe Beach
4.87 out of 5 average rating, 39 reviews

Baybreeze @ Buckroe -hot tub, sauna, game rm. 5bd

JosephRating, 5 stars2 weeks ago
Rachel’s 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! There’s 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! Let’s 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 couldn’t wait to hit the hay that night! This place is worth every penny.
Guest favorite
A three-story condo building is portrayed, featuring balconies and a facade with beige siding and dark red shutters. A snow-dusted lawn surrounds the structure, while a paved walkway leads to the entrance, providing accessibility and a welcoming approach.
Condo in Williamsburg
5 out of 5 average rating, 11 reviews

Wyndham Governor's Green (3 BD Deluxe)

GlennRating, 5 stars4 months ago
Great location, private and peaceful. Staff was very helpful and friendly.
Superhost
A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.
Home in Cape Charles
4.75 out of 5 average rating, 4 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

CatherineRating, 5 stars3 days ago
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!
Superhost
A circular brick fire pit is surrounded by several wooden Adirondack chairs, offering a cozy gathering spot. The well-maintained lawn is dotted with trees, and a building is visible in the background, warmly lit against the evening sky.
Apartment in Williamsburg
4.67 out of 5 average rating, 3 reviews

Patriots Place 2 Bedroom Lockoff

ElizabethRating, 5 stars8 months ago
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.
Top guest favorite
A private Jacuzzi is positioned on a covered porch, surrounded by greenery. LED lights illuminate the water, creating a relaxing atmosphere, while a ceiling fan provides airflow. Adjacent to the hot tub, a clock is mounted on the wall, enhancing the outdoor space.
Guesthouse in Portsmouth
4.97 out of 5 average rating, 198 reviews

Spring Hill Guest Cottage - Portsmouth

EsmeRating, 5 stars1 week ago
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. šŸ’™šŸ’ššŸ©µā¤ļø I can't wait to stay here again. Thank you, Susan and Ron.

House rentals in Chesapeake

Guest favorite
The living room showcases a neutral palette with two cozy sofas and a light-colored coffee table at the center. Wall art adorns the space, complemented by natural light filtering through the windows, creating a relaxed atmosphere perfect for gathering.
Home in Virginia Beach
4.96 out of 5 average rating, 320 reviews

Lakeside Oasis - Walk 2 everything! 3Blocks2Beach

Liz Rating, 5 stars7 months ago
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.
Guest favorite
A spacious living room features a comfortable sectional sofa, a wooden entertainment center with a large TV, and a decorative console table. Light-colored walls complement the area rug, and framed artwork adds interest. A staircase is visible, leading to the upper level.
Home in Norfolk
4.92 out of 5 average rating, 131 reviews

3 bedroom private home a block from the beach!

JennRating, 5 stars3 weeks ago
Kate’s place was perfect for our family’s 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 — 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!
Guest favorite
Home in Buckroe Beach
4.91 out of 5 average rating, 110 reviews

3 bedroom home minutes from Buckroe Beach

CiaraRating, 5 stars1 month ago
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.
Guest favorite
An open and inviting living area features two sofas in blue and gray, complemented by a light wooden coffee table. Natural light filters through large windows, highlighting the subtle wall art and a mix of seating options including stylish chairs and a lamp.
Home in Virginia Beach
4.94 out of 5 average rating, 114 reviews

Lakefront House @ Oceanfront

CelestineRating, 5 stars8 months ago
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!
Guest favorite
The covered porch features a seating area with two white chairs and a small table, surrounded by hanging flower baskets. The front door is framed by large windows, allowing natural light into the space. Lush trees are visible in the background.
Home in Moyock
4.86 out of 5 average rating, 113 reviews

Cozy Country Cottage

CrystalRating, 5 stars2 months ago
Nice quite location
Guest favorite
A charming two-story beach house is presented with yellow siding and blue shutters. A white picket fence surrounds the front yard, while fish-shaped decorations adorn the exterior. A welcoming porch features a green front door, inviting guests to relax in the coastal atmosphere.
Home in Cape Charles
4.93 out of 5 average rating, 201 reviews

Charming house close to beach and shops!

MitziRating, 5 stars3 months ago
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!
Top guest favorite
The exterior view of the beach home showcases a charming two-story structure with a shingle facade. A well-maintained pathway leads to the entrance, surrounded by landscaped plants and a spacious driveway accommodating two vehicles. A deck is visible above, offering potential outdoor relaxation areas.
Home in Virginia Beach
4.99 out of 5 average rating, 190 reviews

Play by the Bay 1 MIN TO WATER

JayRating, 5 stars2 weeks ago
We had a wonderful stay at Diana’s 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 incredible—from 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!
Superhost
A balcony area features two brightly colored chairs, one blue and one red, positioned on a wooden deck. The view includes tree-lined surroundings and a quiet street, emphasizing a tranquil outdoor space.
Home in Virginia Beach
4.8 out of 5 average rating, 145 reviews

Chesapeake Bay Beach house (Chic’s Beach) 1 block!

KiovenyRating, 5 stars8 months ago
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 didn’t get to use the bbq grill but next time we stay here we will. Beautiful home. Thank you

House rentals with jacuzzis in Chesapeake

Guest favorite
Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.
Home in Portsmouth
4.94 out of 5 average rating, 108 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

JustinRating, 5 stars1 week ago
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!
Guest favorite
A four-person hot tub is illuminated with blue light, set within a cozy space featuring string lights overhead. Large windows with decorative shutters provide natural light, while a comfortable swing chair is positioned nearby, enhancing the relaxation area.
Home in Newport News
4.92 out of 5 average rating, 76 reviews

1-Bedroom Home Near Christopher Newport University

EmilyRating, 5 stars2 weeks ago
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!
Guest favorite
A spacious hot tub is situated on the deck, overlooking the vast expanse of the water. The tranquil surface ripples under the cloudy sky, creating a serene ambiance. A black lounge chair is positioned nearby, inviting relaxation while enjoying the captivating views.
Home in Buckroe Beach
4.96 out of 5 average rating, 77 reviews

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

MikeRating, 5 stars1 week ago
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.
Top guest favorite
An open floor plan kitchen is highlighted with stone countertops and stainless steel appliances. Natural light enters through large sliding doors, connecting indoor and outdoor areas. Stylish seating is arranged in the living space, featuring a cozy chair and decorative elements on the walls.
Home in Corolla
4.99 out of 5 average rating, 84 reviews

Coral Cove- Backyard-Hot Tub-Walk to beach-Dogs ok

TriciaRating, 5 stars1 week ago
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.
Top guest favorite
A hot tub is displayed, featuring a clean water surface with gentle ripples. The surrounding area is enclosed by wooden fencing and green foliage is visible in the background, providing a sense of privacy and tranquility.
Home in Corolla
5 out of 5 average rating, 16 reviews

Splash of Lime Carova 4x4 Beach Cottage

Mindy StewartRating, 5 stars5 days ago
Martin’s 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 Martin’s 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!! 😁
Superhost
A spacious living area features a large blue sectional sofa arranged around a white coffee table with decorative detailing. Natural light floods the room through large windows, highlighting the coastal views and the wooden ceiling with exposed beams.
Home in Corolla
4.93 out of 5 average rating, 30 reviews

Bright 5BR3.5BA Sleeps 12 Hot tub Close to Beach

LaurenRating, 5 stars9 months ago
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!
Guest favorite
A two-story blue beach house is showcased with white railings and large windows. A spacious porch with chairs is visible, and a large umbrella provides shade. A vibrant red star adorns the house's front. An accessible driveway leads to a vehicle parked beside the entrance.
Home in Corolla
4.88 out of 5 average rating, 52 reviews

7 Bedroom | Corolla Light Resort | Private Pool &

JenniferRating, 5 stars5 months ago
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.
Guest favorite
A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.
Home in Knotts Island
4.95 out of 5 average rating, 112 reviews

Island Lotus Yoga & Spa

CallieRating, 5 stars2 weeks ago
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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