Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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

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Guest favourite

Guest suite in Virginia Beach

4.97 out of 5 average rating, 233 reviews

Scott's Garden Suite At The Crooked House

Just blocks from the beach, Scott's Garden Suite is nestled in the back yard of one of southside's desireable neighborhoods. With a spacious, queen bedroom & small reading/sleeping den, this little private hideaway is ideal for 2/3 adults or small family. Adjacent to the ViBe Art District/restaurants/shopping, it has kitchenette, 3/4 bath & outdoor LR with gas fire table. This is a ‘homeshare’ SRT & is within the in-resident owners’ home - separately entranced & private for convenience/safety.

Sep. 19 – 26

$179 CAD per night

Guest favourite

Guest suite in Chesapeake

4.97 out of 5 average rating, 235 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!

Jul. 23 – 30

$209 CAD per night

Guest favourite

Guesthouse in Norfolk

4.98 out of 5 average rating, 552 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.

Nov. 6 – 13

$220 CAD per night

Guest favourite

Guest suite in Chesapeake

4.95 out of 5 average rating, 475 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.

Nov. 18 – 25

$193 CAD per night

Guest favourite

Villa in Norfolk

4.95 out of 5 average rating, 134 reviews

8 minutes walking from Sarah Constant Beach Park

Our beach home is located just an 8-minute walk from Sarah Constant Beach Park, the Ocean View Fishing Pier Restaurant. The Ocean View Shopping Center is also just an 8-minute walk away. You'll find numerous restaurants supermarket all within easy walking distance. The Norfolk Navy station is just a 5-minute drive away. Our single-family home features a huge backyard, 3 bedrooms, and 2 bathrooms. Our home is a very quiet and safe place, and parties are not allowed. We are pet friendly!

Feb. 20 – 27

$212 CAD per night

Guest favourite

Townhouse in Chesapeake

4.88 out of 5 average rating, 109 reviews

2BR-1.5 Bath Electric & Vibrant R&R Townhome

Listing description Kick back & relax in this calm, stylish space. 1600 sq ft stunning renovated & designed townhome! -Skip the traffic; 15 min drive to most of Hampton Roads, beaches; 3 mins from restaurants, groceries & more -Free parking -Optimal cleaning 100% disinfected space -2 bedrooms -Comfortable 2 Queen Beds & 1 Full Futon -1.5 baths with high end, modern finishes -Outdoor back private patio seating - Smart home features: keyless access cord + living room TV with roku

Jul. 10 – 17

$307 CAD per night

Guest favourite

Townhouse in Chesapeake

4.9 out of 5 average rating, 101 reviews

Family friendly townhouse

A perfect place to stay when you can't be at home! Townhouse located in lovely family friendly neighborhood. Only a 20-30 min drive to NOB, Portsmouth Naval Shipyard and Oceana. Bright open kitchen with everything you need. Large living room with new comfortable couch and large Smart TV to hang out and watch tv. Privacy fenced back yard to sit and enjoy the evening or a morning cup of coffee. Large master bedroom with full bath and tiled shower. Washer and dryer in the home.

Sep. 30 – Oct. 7

$302 CAD per night

Guest favourite

Apartment in Chesapeake

4.95 out of 5 average rating, 41 reviews

Blissful Nook @ Washington

This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor above the car garage. While relaxing or vacationing just know that this apartment is centrally located to Virginia Beach Oceanfront, Outer banks N.C. museums, Colonial Williamsburg, Busch garden, Water Country USA and many restaurant. This apartment is attached to the main home with a dedicated private entrance. This location is safe and private for our guest.

Jun. 11 – 18

$201 CAD per night

Guest favourite

Place to stay in Virginia Beach

4.99 out of 5 average rating, 112 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. We do our best to provide the comforts of home. -mini fridge -water filter -coffee bar -beach towels -folding chairs -beach blanket -sound machine -and more We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

Jan. 1 – 8

$212 CAD per night

Guest favourite

Guest suite in Norfolk

4.93 out of 5 average rating, 215 reviews

Cobblestone street apartment with rooftop views!

Historic, Downtown area of Norfolk. Walking distance to shops, restaurants, museums, landmarks, parks, memorials, EVMS, & CHKD. This special residence is on the National Register of Historic Homes, includes a clawfoot tub & rooftop patio (no hold harm). This High Victorian Italian home was built in 1870, with a Mansard roof & features an ornamental cast iron veranda. John Cary Weston built this as a summer residence following the Civil War.

Sep. 17 – 24

$233 CAD per night

Guest favourite

Guesthouse in Chesapeake

4.98 out of 5 average rating, 214 reviews

Beautiful and Chic, One Room 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.

Jan. 22 – 29

$153 CAD per night

Guest favourite

Guest suite in Virginia Beach

4.92 out of 5 average rating, 237 reviews

Cozy Private Studio

Cozy inviting Efficiency Apartment located in the heart of Virginia Beach! Minutes from highway 64. Which gives easy access to anywhere in the Hampton Roads area. 15-20 minute drive to Virginia Beach Ocean front and convention center. 2 minutes from CBN and founders in. Soccer complex, Stumpy lake golf course close by. Restaurants and shopping 5 minutes away.

Oct. 3 – 10

$163 CAD per night