Chesapeake vacation rentals

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Popular amenities for Chesapeake vacation rentals

House rentals in Chesapeake

Guest favorite
A light-filled living area features a comfortable sectional sofa and a coffee table centered on a textured rug. Adjacent, a dining table accommodates several chairs, while a wall-mounted television is positioned above a decorative fireplace. Windows provide views of the outdoor space.
Home in Chesapeake
4.92 out of 5 average rating, 38 reviews

Beautiful home in Chesapeake

MelindaRating, 5 stars3 weeks ago
This home was very clean, accurate to the photos, and very comfortable. We really appreciated the fully fenced in backyard for our dog. The location was close to a mall, restaurants, supermarkets, and Virginia Beach. The neighborhood was very family friendly and safe. We would definitely stay here again if in the area.
Top guest favorite
A bright living area features a large flat-screen television mounted on the wall and a comfortable seating arrangement. Large sliding doors open to a view of the water outside, while a soft area rug adds warmth to the space.
Home in Portsmouth
4.95 out of 5 average rating, 59 reviews

R & R River House

JacquelineRating, 5 stars2 days ago
Our stay was really nice. The townhouse was beautiful and very clean. It had all the necessary amenities anyone could ask for. It was centrally located to all the places we wanted to see and we enjoyed how we felt at home from the minute we walked in. We would definitely stay there again.
Superhost
A modern kitchen is highlighted by a spacious island featuring four wooden bar stools. Natural light filters through sheer curtains, illuminating the sleek cabinetry and white countertops. A stylish centerpiece is positioned on the island, complementing the contemporary design.
Home in Chesapeake
4.93 out of 5 average rating, 57 reviews

Chesapeake Haven - Relaxing Space + Lux Kitchen

JoshuaRating, 5 stars1 week ago
My family and I had a wonderful stay at this lovely Airbnb! The house was spotless, cozy, and felt just like home. Everything was thoughtfully prepared, from the comfortable bed to the little touches that made the space warm and inviting. The host was kind and responsive, making the whole experience easy and relaxing. I’d definitely stay here again—highly recommend!
Guest favorite
A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.
Home in Norfolk
4.99 out of 5 average rating, 100 reviews

Ghent on the Corner: Cozy 3 bed 2.5 bath home

RuthieRating, 5 stars1 month ago
If you're looking for a thoughtful host, a well-run place and a cozy stay, Abel's place is the place to go! The house is so beautiful, well taken care of and fully equipped. Abel is so friendly, a reliable host and quick to respond if you ever have any questions regarding the house. My stay here was above my expectations. Abel is absolutely an amazing host, and I had a great time at this place! It was perfect and I really enjoyed my time here. I would definitely go back to this place again, and I highly recommend it.
Guest favorite
A living area features a dark sectional sofa with a decorative pillow and a coffee table with a patterned surface. A soft area rug covers the hardwood floor. Light flows in through glass doors that lead to an outdoor space, while ceiling fans provide additional comfort.
Home in East Ocean View
4.92 out of 5 average rating, 191 reviews

@Whit’s End? Come in and Relax

MicheleRating, 5 stars1 week ago
the house and fenced yard worked perfectly for our family vacation. We brought our 2 English cream retrieversand the set up for the back yard was perfect. Our son plays piano so having a piano in the house made it extra special. I would definitely stay here again.
Top guest favorite
A beach scene at sunset features individuals playing volleyball in the sand. The calm water reflects shades of pink and orange from the setting sun. Silhouettes of a pier and distant structures are visible along the horizon, framed by beach grass in the foreground.
Home in Virginia Beach
4.92 out of 5 average rating, 256 reviews

Quilted Quarters by the Bay with Private Entrance

ElizabethRating, 5 stars1 day ago
Audrey’s quilted corners by the bay was perfect for a peaceful, relaxation vacation with my sister. We enjoyed being close to the quiet, peaceful beachfront and the bike/walking path into the state park. Highly recommend for a relaxing virginia beach experience. When we experienced issues with bugs entering the room (which is a very normal occurrence in the southern climate especially in the rain), Audrey quickly contacted us and eased our minds by spraying for bugs inside the room and outside the house. Audrey did everything she could to help. Be aware of the possibility of bugs given the nature of the climate and more wooded, residential area. Overall, we really enjoyed our stay.
Guest favorite
A charming white home with turquoise accents captures attention with its distinctive architectural style. Lush greenery surrounds the property, enhancing its curb appeal. A neatly paved walkway leads to the inviting entrance, while a driveway is visible, providing convenient access to the garage.
Home in Norfolk
4.85 out of 5 average rating, 157 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

SaraRating, 5 stars2 weeks ago
Adam's place was a great find! Beautiful home..loved the decorations. Made our stay in Norfolk just like home and enjoyable..will be back again soon!
Guest favorite
A dining area features a sleek wooden table surrounded by six chairs. Above, a chandelier provides soft lighting. The space connects to a well-lit living area visible in the background, with a modern recliner and additional furnishings enhancing the room's functionality.
Home in Chesapeake
4.95 out of 5 average rating, 22 reviews

Simply Amazing in Chesapeake

DeborahRating, 5 stars2 weeks ago
Sereva made us feel welcome and valued from the moment we first contacted her. The home was beautiful, sparkling clean, and lovely. We enjoyed every minute of our stay and she was always available to answer questions. Thank you for being a wonderful, welcoming host!

Other great vacation rentals in Chesapeake

Superhost
A rustic wooden door with a sliding mechanism is positioned next to a framed sign that reads 'LIVE simply.' A wall-mounted planter holds a small arrangement of greenery, complementing the warm wood tones of the dining chairs and table in the scene.
Apartment in Chesapeake
4.91 out of 5 average rating, 129 reviews

2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.

EmilyRating, 5 stars1 week ago
We had a wonderful stay! The house was spotless and comfortable. Our hosts provided some snacks and water which was so appreciated after a long drive with our baby. We have family in the area and would absolutely stay again next time we visit!
Top guest favorite
A wooden playground structure features a green slide extending downward. In the image, a child is seen sliding down. Surrounding the playground are natural wooded areas, with additional outdoor play equipment visible in the background.
Guesthouse in Chesapeake
4.98 out of 5 average rating, 44 reviews

Country Escape - Next DOOR - Hidden Gem

MichaelRating, 5 stars2 weeks ago
The lodging was great! Very clean, and so tastfully and creatively decorated. Tracy had "everything" you would need, extra batteries, spices, blankets, toiletries, and much much more....oh and games of course. We stayed 2 nights for a grandaughter's wedding. Stayed with our daughter, husband, and 2 children. It even has laundry detergent for the washer and dryer. The beds were comfortable and temperature controls worked great. We loved it. Thank you.
Top guest favorite
A covered outdoor patio is framed by white pillars and features several cozy seating options. The brick flooring is complemented by lush greenery, creating a calm space. Stairs lead down to the surrounding yard, enhancing accessibility to the outdoor area.
Guesthouse in Chuckatuck
4.98 out of 5 average rating, 125 reviews

Country Living Guest House (Upstairs/Downstairs)

BriRating, 5 stars1 week ago
We booked Willis's guest house for my friend's birthday celebration. She wanted a laid back, relaxing weekend & that's exactly what we experienced! The hot tub was amazing. We enjoyed walking the land & seeing all the chicken. We used the full kitchen to cook a wonderful dinner. And the hosts were sooo welcoming. We felt right at home. We hope to come back soon!
Top guest favorite
Apartment in Chesapeake
4.97 out of 5 average rating, 73 reviews

Entire Apartment - No Cleaning Fees!

Brandi Rating, 5 stars4 weeks ago
Listen, this house is the house you want to stay at instead of a hotel lol me & my 2 year old stayed here & it just felt like home. The house looks exactly like the pictures, and don’t get me started on the bed, I slept like a baby, it was like being on a cloud, I kid you not lol. Jamey was so nice & answered and responded quickly. it’s a quiet neighborhood, everything is close far as food & shopping. I would definitely recommend staying here to anyone.
Guest favorite
A spacious living area is defined by a light grey sectional sofa, featuring a yellow and white striped decorative pillow. The open kitchen, equipped with stainless steel appliances, is visible in the background, enhancing the functional layout. Soft natural light illuminates the room through sheer curtains.
Apartment in Great Bridge
4.96 out of 5 average rating, 75 reviews

Blissful Nook @ Washington

TariqRating, 5 stars6 days ago
This was an extremely satisfying stay. The place looks like the photos, but arriving in person really shows the coziness of the rooms. Great atmosphere within a private space with all the amenities necessary during an extended stay. Absolutely loved and would recommend.
Guest favorite
A serene beach scene showcases soft sand and gentle sea grass, with a beautiful sunset illuminating the sky in shades of orange and purple. The calm water reflects the colors, while silhouettes of two people can be seen in the distance near the water's edge.
Guest suite in Virginia Beach
4.9 out of 5 average rating, 641 reviews

Quiet Neighborhood 7 Miles From the Beaches

Natasha J.Rating, 5 starstoday
Had a wonderful stay at Mona's place. We were in town for a softball tournament and her place was perfect for our visit. Close to fields, beaches, and restaurants. Mona was so nice and helpful. Wish we could have stayed longer her place was so peaceful, spacious and super clean. We would definitely return.
Top guest favorite
The image captures a serene view of the water at sunset, with vibrant orange and purple hues reflecting on the surface. Soft waves create a gentle ripple effect, while clouds in the sky add dimension to the scene.
Cottage in Norfolk
5 out of 5 average rating, 271 reviews

Beautiful Cottage Waterfront Near Downtown Norfolk

MichaelRating, 5 stars1 month ago
My wife and I have been using Airbnb for about 10 years now. This is our absolute favorite place. The cottage is very clean. It is in a great location (between downtown Norfolk and Virginia Beach) in a quiet neighborhood right on the Elizabeth River. Michael and Andy a very quick to respond to any questions with great recommendations. It is the little things, like leaving snacks and drinks (which came in handy after long hikes) to Andy greeting us at check-in that made us feel welcomed and comfortable. We cannot wait to come back again
Guest favorite
The image shows a charming exterior corner of the building featuring a large bay window framed by dark shutters. A landscaped area surrounds the window, with plants and a small pond integrated into the stone retaining wall.
Guest suite in Virginia Beach
4.85 out of 5 average rating, 440 reviews

Guest Suite Studio w/ Kitchenette & Private bath.

ChristinaRating, 5 stars1 month ago
It was exactly as depicted and perfect for a quick getaway.

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 110 vacation rentals in Salem, over 110 vacation rentals in Lynnhaven, over 500 vacation rentals in Downtown Norfolk, over 270 vacation rentals in Ghent, and over 500 vacation rentals in Olde Towne.

  • 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 guesthouse rentals in Chesapeake?

    Experience the best of Chesapeake with our guesthouse rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 condo rentals in Chesapeake?

    Chesapeake has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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