Chesapeake vacation rentals

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Top-rated vacation rentals in Chesapeake

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

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Guest favorite

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 16 – 23

€ 125 per night

Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 200 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Dec 7 – 14

€ 125 per night

Guest favorite

Guest suite in Chesapeake

4.97 out of 5 average rating, 234 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

€ 144 per night

Guest favorite

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.

Dec 3 – 10

€ 152 per night

Guest favorite

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.

Feb 5 – 12

€ 133 per night

Guest favorite

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

Sep 13 – 20

€ 212 per night

Guest favorite

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.

Aug 27 – Sep 3

€ 229 per night

Guest favorite

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 5 – 12

€ 143 per night

Guest favorite

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.

Nov 2 – 9

€ 160 per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 206 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Nov 28 – Dec 5

€ 97 per night

Guest favorite

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

€ 105 per night

Superhost

Apartment in Portsmouth

4.84 out of 5 average rating, 293 reviews

Spacious 2 bedroom apt in Historic Port Norfolk

If you enjoy homes with lots of history and modern touches, this is the place for you! Our lovely Victorian home was built in the year 1900. We’ve been enjoying all its old world charms since we purchased it in 2016, and we are thrilled to share a part of it with you on your vacations and journeys to exciting new destinations!

Sep 3 – 10

€ 111 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesapeake vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Chesapeake's top sights

Veterans United Home Loans Amphitheater at Virginia Beach56 locals recommend

Mount Trashmore Park83 locals recommend

Lynnhaven Mall99 locals recommend

MacArthur Center154 locals recommend

The NorVa47 locals recommend

Greenbrier Mall25 locals recommend

Other great vacation rentals in Chesapeake

Guest favorite

Home in Norfolk

4.92 out of 5 average rating, 152 reviews

@Whit’s End? Come in and Relax

Jan 12 – 19

€ 116 per night

Guest favorite