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, 236 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 2 – 9

R2,281 ZAR per night

Guest favorite

Apartment in Newport News

4.97 out of 5 average rating, 148 reviews

Centrally Located Sleek Studio Apartment

Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.

Jan 10 – 17

R1,623 ZAR per night

Guest favorite

Guest suite in Chesapeake

4.97 out of 5 average rating, 236 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!

Oct 2 – 9

R2,421 ZAR per night

Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 554 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 14 – 21

R2,386 ZAR per night

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 479 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 25 – Mar 4

R2,106 ZAR per night

Guest favorite

Townhouse in Chesapeake

4.88 out of 5 average rating, 111 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

Jun 4 – 11

R3,385 ZAR per night

Guest favorite

Townhouse in Chesapeake

4.9 out of 5 average rating, 103 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.

Oct 5 – 12

R2,731 ZAR per night

Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 288 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. (Please also check out our additional property "The Water's Edge"). Sun, Se and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house is located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High speed fiber-optic wifi and cable with blue ray player provided.

Oct 16 – 23

R2,488 ZAR per night

Guest favorite

Place to stay in Virginia Beach

4.99 out of 5 average rating, 116 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!

Nov 12 – 19

R2,321 ZAR per night

Guest favorite

Guesthouse in Chesapeake

4.98 out of 5 average rating, 216 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.

Oct 12 – 19

R1,621 ZAR per night

Superhost

Tiny home in Chesapeake

4.84 out of 5 average rating, 128 reviews

Rural Tiny House in the Edge Of the Woods

Self Check in, King size bed, Tiny House on the corner of a 10 Acre Property with a few Angus Cows. Hosting family house is near by. Feel free to walk the property and the neighborhood roads. Located on the North Edge of the Great Dismal Swamp. Enjoy a fire in the fire pit on the back deck, a sunset from the front porch and the hammock in the woods.

Sep 2 – 9

R2,674 ZAR per night

Guest favorite

Townhouse in Chesapeake

4.92 out of 5 average rating, 109 reviews

Tasha's Townhouse *King, Queen, Twin*

Centrally-located townhouse in the popular greenbrier area. Walking distance to park, lake, restaurants and shops. This cozy and beautiful home is thoughtfully crafted to provide a space that feels as authentic as you are. Centrally located to highways with quick access to military bases and downtown Portsmouth/Norfolk.

Aug 4 – 11

R3,803 ZAR 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

Apartment in Williamsburg

4.84 out of 5 average rating, 361 reviews

The Nook

Sep 9 – 16

R1,833 ZAR per night

Guest favorite

Guest suite in Chesapeake

4.99 out of 5 average rating, 136 reviews

Beautiful Two Bedroom King Bed Guest House

Jul 16 – 23

R5,558 ZAR per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 209 reviews

Quilted Quarters by the Bay with Private Entrance

Jan 23 – 30

R1,613 ZAR per night

Guest favorite

Home in Norfolk

4.92 out of 5 average rating, 155 reviews

@Whit’s End? Come in and Relax

Oct 12 – 19

R1,605 ZAR per night

Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 205 reviews

Mason Manor - Downtown Smithfield next to WCP

Dec 17 – 24

R2,099 ZAR per night

Guest favorite

Guesthouse in Yorktown

4.97 out of 5 average rating, 203 reviews

Charming Yorktown Battlefield Cottage

Oct 7 – 14

R1,888 ZAR per night

Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 241 reviews

Cozy Ground Floor Apt in Historic Home

Nov 7 – 14

R1,892 ZAR per night

Guest favorite

Guest suite in Virginia Beach

4.85 out of 5 average rating, 356 reviews

Guest Suite Studio w/ Kitchenette & Private bath.

Jun 13 – 20

R2,808 ZAR per night

Show all

Other great vacation rentals in Chesapeake

Guest favorite

Guest suite in Virginia Beach

4.99 out of 5 average rating, 311 reviews

Just Steps Away to the Beach

Aug 18 – 25

R2,883 ZAR per night

Guest favorite

Guest suite in Virginia Beach

4.91 out of 5 average rating, 206 reviews

Rest A’Shore-Virginia Beach

Oct 10 – 17

R2,336 ZAR per night

Guest favorite

Cottage in Norfolk

4.98 out of 5 average rating, 176 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Mar 17 – 24

R3,796 ZAR per night

Guest favorite

Farm stay in Cape Charles

5.0 out of 5 average rating, 333 reviews

Private Guesthouse on Secluded Waterfront Farm

Sep 17 – 24

R3,311 ZAR per night

Guest favorite

Guesthouse in Coinjock

4.99 out of 5 average rating, 301 reviews

Church's Island Carriage House

Apr 20 – 27

R3,431 ZAR per night

Guest favorite

Apartment in Virginia Beach

4.91 out of 5 average rating, 232 reviews

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

Feb 10 – 17

R2,097 ZAR per night

Guest favorite

Cottage in Norfolk

5.0 out of 5 average rating, 250 reviews

Beautiful Cottage Waterfront Near Downtown Norfolk

Aug 8 – 15

R4,363 ZAR per night

Guest favorite

Apartment in Hampton

4.97 out of 5 average rating, 127 reviews

Downtown Hampton's Hidden Gem with Queen Bed

May 18 – 25

R2,263 ZAR per night

Show all

Quick stats about vacation rentals in Chesapeake

Total rentals
1.1K properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Rentals with a pool
150 properties have a pool
Pet-friendly rentals
340 properties allow pets
Family-friendly rentals
510 properties are a good fit for families
Total number of reviews
31K reviews

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 550 vacation rentals in Olde Towne, over 320 vacation rentals in Ghent, over 550 vacation rentals in Downtown Norfolk, 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 590 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 340 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 150 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 $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 120 house 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 60 house rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Chesapeake have wifi?
Absolutely! We offer over 20 guesthouse rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chesapeake have self check-in?
Absolutely! We offer over 160 house rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly townhouse rentals in Chesapeake?
Chesapeake has more than 70 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Chesapeake vacation rentals

Top-rated vacation rentals in Chesapeake

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Chesapeake vacation rentals

Stay near Chesapeake's top sights

Other great vacation rentals in Chesapeake

Apartment in Williamsburg

Guest suite in Chesapeake

Home in Virginia Beach

Home in Norfolk

Home in Smithfield

Guesthouse in Yorktown

Apartment in Portsmouth

Guest suite in Virginia Beach

Other great vacation rentals in Chesapeake

Guest suite in Virginia Beach

Guest suite in Virginia Beach

Cottage in Norfolk

Farm stay in Cape Charles

Guesthouse in Coinjock

Apartment in Virginia Beach

Cottage in Norfolk

Apartment in Hampton

Quick stats about vacation rentals in Chesapeake

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Chesapeake?

Are there vacation rentals with a dedicated workspace in Chesapeake?

Are there pet-friendly vacation rentals in Chesapeake?

Are there Chesapeake vacation rentals on Airbnb with pools?

How much does it cost to stay in rv rentals in Chesapeake?

Do house rentals in Chesapeake have a bbq area?

Do house rentals in Chesapeake have a gym?

Do guesthouse rentals in Chesapeake have wifi?

Do house rentals in Chesapeake have self check-in?

Are there family-friendly townhouse rentals in Chesapeake?

Destinations to explore