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Vacation rentals in Chesapeake

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chesapeake

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

Guest suite in Virginia Beach

4.9 out of 5 average rating, 679 reviews

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Top guest favorite

The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.

Guest suite in Chesapeake

4.96 out of 5 average rating, 335 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

A cozy living area is furnished with a beige sofa and a blue armchair. A coffee table with a decorative runner sits in front, surrounded by wooden paneling. Natural light enters from a nearby window, complemented by patterned curtains. Wall art adds subtle character to the space.

Apartment in Portsmouth

4.96 out of 5 average rating, 137 reviews

"The Ponderosa B" - Close to the Casino & Concerts

Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood about 1/2 mile Rivers Casino! -, Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth 5.9 miles to Norfolk, 22 mi to VB Oceanfront.

Top guest favorite

A wooden deck extends over the water, featuring a small round table and two chairs. Petunias bloom in a planter nearby, and the calm surface of the river reflects the clear blue sky. Lush green trees line the opposite shore, enhancing the peaceful view.

Cottage in Norfolk

5 out of 5 average rating, 287 reviews

Beautiful Cottage Waterfront Near Downtown Norfolk

A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

Top guest favorite

A bright sleeping area features a spacious bed with light blankets, accented by a decorative throw. A large circular window allows natural light to fill the space, complemented by dark curtains. A cozy armchair sits nearby, enhancing the room's inviting ambiance.

Guesthouse in Ghent

4.97 out of 5 average rating, 654 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Top guest favorite

A spacious guest suite features a large bed with layered bedding, accompanied by a cozy green throw. A vibrant area rug enhances the room's warmth, while a small table and chair provide a work or relaxation space. A kitchenette area is visible in the background.

Place to stay in Virginia Beach

4.99 out of 5 average rating, 195 reviews

Salty Willow-a “suite retreat” in the heart of VB!

We love welcoming people to our home in the heart of Virginia Beach! Come and go as you please in our guest suite with a separate entrance and privacy latches-no one will enter your space. You will also have the added convenience of having the host family on site. We do our best to provide the comforts of home. -fridge/freezer -beach essentials -toaster -coffee bar -extra essentials We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

A dining area features a wooden table set for six, accompanied by cross-back chairs. A standing lamp casts soft light. Large windows above allow natural light to illuminate the space, while a few pieces of artwork add a splash of color to the walls.

Apartment in Chesapeake

4.99 out of 5 average rating, 168 reviews

Modern Luxury Peace & Quiet.

Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Top guest favorite

A cozy bedroom features a four-poster bed adorned with soft linens and decorative pillows. A vintage armchair is positioned nearby, while a window dressed with light blue curtains allows natural light to brighten the space. Subtle wall stripes in calming colors add character.

Home in Chesapeake

4.96 out of 5 average rating, 109 reviews

Cook's Country Escape - House nestled in woods

Escape your day to day life to enjoy this house in the country. This countryside home will be great for you, your family and/or friends to be away from the city life yet close to a lot of destinations. We are 1/2 way in between VA Beach and OBX, NC so many guests will visit while they are in the area. This home is quaint like a cabin but has all the house amenities. From the moment you walk in, you will feel the warmth and comfort of a country home to enjoy and relax in during your stay.

The exterior of a private attached suite is shown, featuring a welcoming entrance with white steps and a small porch. Lush greenery and colorful flowers frame the walkway, leading to a paved driveway. A wooden fence provides privacy, while a well-maintained lawn enhances the setting.

Guest suite in Chesapeake

4.95 out of 5 average rating, 591 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

A spacious room features a king-size bed with a soft white bedspread and dark accent pillows. A seating area with a leather futon and dining table for four is present. Natural light enters through a large window, complemented by dark curtains. A small fridge is positioned nearby.

Guest suite in Chesapeake

4.92 out of 5 average rating, 295 reviews

King Guest Suite - A Family Vacation Rental

Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!

A comfortable living area is furnished with a plush sofa and an accent chair. A large television is mounted on the wall, and a decorative sign above adds a touch of character. Light wood cabinets are visible in the background, enhancing a spacious feel.

Apartment in Chesapeake

4.91 out of 5 average rating, 139 reviews

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

Welcome to Casa de Curtin This apartment features a full kitchen w/ dbl sink, refrigerator, washer, dryer, range, microwave, Keurig, table & chairs. The living room has a plush, oversized sofa & chair set & two 4K smart tvs & fast WiFi. Br’s have a King & Queen comfortable beds and ceiling fans and there is a large full bth w/ walk-in shower and vent fan. Smart locks make self check-in a breeze! Located close to VA Beach.

Top guest favorite

The exterior of a two-story brick apartment building is shown, featuring a staircase leading to the entrance. Lush green shrubs and trees frame the entrance, while a driveway accommodates two blue recycling bins. A neighboring structure is visible to the left.

Guesthouse in Chesapeake

4.98 out of 5 average rating, 248 reviews

Beautiful and Chic Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Chesapeake vacation rentals

Laptop-friendly workspace

Chesapeake oceanfront vacation rentals

A view of the ocean from a living area is presented through sliding glass doors. Natural light fills the space, enhancing the sea view. The patio features a railing and two outdoor chairs, inviting relaxation while taking in the coastal scenery.

Condo in Virginia Beach

4.82 out of 5 average rating, 303 reviews

Beautiful Beachfront Condo

Top guest favorite

An aerial view captures a coastal neighborhood with sandy beach access along the Chesapeake Bay. Several homes are seen lining the shore, while a small lake is visible in the background. A road runs parallel to the beach, providing access to the surrounding area.

Home in Chic's Beach

4.97 out of 5 average rating, 146 reviews

Water Oaks at Chic's Beach

An aerial view showcases a private beach beside a rectangular saltwater pool, surrounded by open grassy areas, perfect for outdoor activities. The landscape features a clear path leading from the property to the beach, with residential buildings on one side.

Cottage in Bayview

4.97 out of 5 average rating, 264 reviews

Positano Villa

Top guest favorite

A modern living room features a gray sofa adorned with decorative pillows, paired with a light blue coffee table. Two lamps provide ambient lighting. Artwork of coastal scenes decorates the walls, while a patterned area rug enhances the room's coastal theme.

Condo in Virginia Beach

4.99 out of 5 average rating, 124 reviews

Tropical 2BR Condo Getaway 1 Block from the Beach!

Home in Chic's Beach

4.93 out of 5 average rating, 171 reviews

Steps to Beach at Chics Beach! Sleeps 12 & Garage!

Top guest favorite

The image captures a serene beach scene at sunset, with soft pink and orange hues reflecting off calm waters. The sandy shoreline features gentle dunes and sparse vegetation, creating an inviting atmosphere for relaxation and contemplation.

Home in East Ocean View

4.92 out of 5 average rating, 374 reviews

New Beach Home on the Chesapeake Bay

Top guest favorite

Cottage in Bayview

4.99 out of 5 average rating, 144 reviews

Private Beach Access at The OV Beach House

A view from the property showcases the sandy beach and the Atlantic Ocean, with a few beachgoers visible in the distance. Nearby, a low-rise building with balconies and parked cars can be seen, providing a sense of proximity to the shore.

Condo in Sandbridge

4.93 out of 5 average rating, 139 reviews

Ocean & Bay Views - Local Family Owned & Operated

Other great vacation rentals in Chesapeake

A spacious living area features a soft sectional sofa adorned with decorative pillows. A glass-top coffee table is centered on a patterned rug, flanked by side tables with lamps. Natural light streams through two large windows, complemented by light curtains.

Home in Chesapeake

4.97 out of 5 average rating, 78 reviews

Sleeps 6-8, King bed, 2.5 baths

Top guest favorite

A spacious bedroom is presented with a king bed dressed in neutral bedding. Two bedside tables with lamps flank the bed, complementing the light wood furniture. A designated work space, including a desk and chair, is located nearby. Natural light enters through a window adorned with light curtains.

Apartment in Chesapeake

4.96 out of 5 average rating, 85 reviews

Entire Apartment - No Cleaning Fees!

Top guest favorite

A modern kitchen features light cabinetry and granite countertops, complemented by stainless steel appliances. An island with two stools offers additional seating, and a window allows natural light to brighten the space. Essential kitchen items are neatly arranged on the countertop.

Apartment in Great Bridge

4.97 out of 5 average rating, 90 reviews

Blissful Nook @ Washington

Top 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

4.98 out of 5 average rating, 114 reviews

Ghent on the Corner: Cozy 3 bed 2.5 bath home

Top guest favorite

Two comfortable white Adirondack chairs are positioned on a wooden deck, facing the peaceful expanse of the Chesapeake Bay. The scene includes soft grass in the foreground and a clear sky above, creating a serene viewing spot for enjoying the beach.

Guest suite in East Ocean View

4.93 out of 5 average rating, 603 reviews

Beachfront Exclusive Bay front Suite

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, 275 reviews

Quilted Quarters by the Bay with Private Entrance

A charming cottage is presented with a well-maintained front yard, featuring blooming trees and vibrant flower planters. A covered porch is visible, framed by decorative railings and welcoming steps that lead from a concrete driveway. The surrounding greenery adds a peaceful ambiance.

Cottage in Ocean View

4.97 out of 5 average rating, 347 reviews

Lovely Ocean View Cottage

A brick house is presented, featuring a traditional single-story design. A large front lawn is visible, complemented by trees in the background. The home is accented by a welcoming front door and large windows, with a driveway leading to an attached garage.

Home in Chesapeake

4.93 out of 5 average rating, 27 reviews

Quiet 3/2 beautiful Chesapeake

Quick stats about vacation rentals in Chesapeake

Total rentals
960 properties
Total number of reviews
33K reviews
Family-friendly rentals
440 properties are a good fit for families
Pet-friendly rentals
290 properties allow pets
Rentals with a pool
140 properties have a pool
Rentals with dedicated workspaces
500 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 50 vacation rentals in Great Bridge, over 110 vacation rentals in Salem, and over 110 vacation rentals in Lynnhaven.
Are there vacation rentals with a dedicated workspace in Chesapeake?
Yes! Work meets play with ease at over 500 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 290 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 140 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 rv rentals in Chesapeake?
Experience the best of Chesapeake with our rv rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Chesapeake have a bbq area?
Absolutely! We offer over 10 apartment rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chesapeake have a gym?
Absolutely! We offer over 50 house rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Chesapeake have wifi?
Absolutely! We offer over 80 townhouse rentals with wifi 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 house rentals in Chesapeake?
Chesapeake has more than 280 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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