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, 234 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 10 – 17

G$22,856 GYD per night

Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 203 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 2 – 9

G$23,688 GYD per night

Guest favorite

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!

Aug 19 – 26

G$24,660 GYD per night

Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 553 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 18 – 25

G$26,924 GYD per night

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 478 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.

Dec 26 – Jan 2

G$23,772 GYD per night

Guest favorite

Townhouse in Chesapeake

4.88 out of 5 average rating, 110 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 17 – 24

G$38,205 GYD 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.

Jun 20 – 27

G$33,105 GYD per night

Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 286 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.

Sep 27 – Oct 4

G$28,078 GYD per night

Guest favorite

Place to stay in Virginia Beach

4.99 out of 5 average rating, 114 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 13 – 20

G$21,363 GYD per night

Guest favorite

Guest suite in Norfolk

4.93 out of 5 average rating, 216 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.

Dec 2 – 9

G$26,138 GYD per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 207 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

G$18,207 GYD per night

Guest favorite

Guesthouse in Chesapeake

4.98 out of 5 average rating, 215 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.

Dec 9 – 16

G$18,479 GYD 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 Newport News

4.97 out of 5 average rating, 147 reviews

Centrally Located Sleek Studio Apartment

Jan 6 – 13

G$18,312 GYD per night

Guest favorite

Guest suite in Carrollton

4.98 out of 5 average rating, 160 reviews

2BR 1BA Spacious Guest Suite, Woods & Water Views

Feb 20 – 27

G$21,862 GYD per night

Guest favorite

Guesthouse in Portsmouth

4.97 out of 5 average rating, 151 reviews

Spring Hill Guest Cottage - Portsmouth

Mar 17 – 24

G$32,148 GYD per night

Guest favorite

Apartment in Williamsburg

4.84 out of 5 average rating, 360 reviews

The Nook

Nov 8 – 15

G$20,493 GYD per night

Guest favorite

Home in Norfolk

4.92 out of 5 average rating, 153 reviews

@Whit’s End? Come in and Relax

Apr 9 – 16

G$20,085 GYD per night

Guest favorite

Guesthouse in Yorktown

4.97 out of 5 average rating, 203 reviews

Charming Yorktown Battlefield Cottage

Aug 12 – 19

G$22,382 GYD per night

Guest favorite

Guest suite in Virginia Beach

4.99 out of 5 average rating, 309 reviews

Just Steps Away to the Beach

Jul 21 – 28

G$32,541 GYD per night

Guest favorite

Apartment in Chesapeake

5.0 out of 5 average rating, 29 reviews

Entire Apartment - No Cleaning Fees!

Oct 28 – Nov 4

G$20,201 GYD per night

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Other great vacation rentals in Chesapeake

Guest favorite

Guest suite in Chesapeake

4.91 out of 5 average rating, 46 reviews

Guest Suite with Private entrance & bathroom

Jul 16 – 23

G$22,627 GYD per night

Guest favorite

Home in Chesapeake

4.98 out of 5 average rating, 51 reviews

Cook's Country Escape - House nestled in woods

Mar 31 – Apr 7

G$27,917 GYD per night

Guest favorite

Bungalow in Chesapeake

4.93 out of 5 average rating, 72 reviews

Private and Cozy Bungalow Loaded with Amenities

Jun 26 – Jul 3

G$30,822 GYD per night

Superhost

Guesthouse in Suffolk

4.82 out of 5 average rating, 28 reviews

Lakeside Retreat

May 17 – 24

G$23,559 GYD per night

Guest favorite

Home in Chesapeake

4.92 out of 5 average rating, 38 reviews

Hidden Gem in Chesapeake, Virginia

Dec 13 – 20

G$32,789 GYD per night

Guest favorite

Apartment in Suffolk

5.0 out of 5 average rating, 70 reviews

Country Living Guest House (Upstairs/Downstairs)

Mar 8 – 15

G$22,433 GYD per night

Guest favorite

Apartment in Suffolk

4.97 out of 5 average rating, 29 reviews

One Bedroom Loft in Bridgeport, North Suffolk, VA

Jan 27 – Feb 3

G$28,918 GYD per night

Guest favorite

Apartment in Chesapeake

4.97 out of 5 average rating, 97 reviews

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

Jun 11 – 18

G$31,781 GYD per night

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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 110 vacation rentals in Salem, over 320 vacation rentals in Ghent, over 550 vacation rentals in Downtown Norfolk, and over 550 vacation rentals in Olde Towne.
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 apartment rentals in Chesapeake?
Experience the best of Chesapeake with our apartment rentals, starting at about $10 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 apartment rentals in Chesapeake have a gym?
Absolutely! We offer over 70 apartment rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Chesapeake have wifi?
Absolutely! We offer over 40 condo 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 50 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.

Chesapeake vacation rentals

Top-rated vacation rentals in Chesapeake

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Chesapeake vacation rentals

Stay near Chesapeake's top sights

Other great vacation rentals in Chesapeake

Apartment in Newport News

Guest suite in Carrollton

Guesthouse in Portsmouth

Apartment in Williamsburg

Home in Norfolk

Guesthouse in Yorktown

Guest suite in Virginia Beach

Apartment in Chesapeake

Other great vacation rentals in Chesapeake

Guest suite in Chesapeake

Home in Chesapeake

Bungalow in Chesapeake

Guesthouse in Suffolk

Home in Chesapeake

Apartment in Suffolk

Apartment in Suffolk

Apartment in Chesapeake

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 apartment rentals in Chesapeake?

Do apartment rentals in Chesapeake have a bbq area?

Do apartment rentals in Chesapeake have a gym?

Do condo rentals in Chesapeake have wifi?

Do apartment rentals in Chesapeake have self check-in?

Are there family-friendly condo rentals in Chesapeake?

Destinations to explore