Chesapeake vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chesapeake

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

Guest favorite

Apartment in Newport News

4.97 out of 5 average rating, 143 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.

Nov 16 – 23

G$18,385 GYD per night
Guest favorite

Guest suite in Chesapeake

4.97 out of 5 average rating, 227 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!

Jun 8 – 15

G$19,965 GYD per night
Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 549 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.

Sep 27 – Oct 4

G$27,031 GYD per night

Popular amenities for Chesapeake vacation rentals

Stay near Chesapeake's top sights

Veterans United Home Loans Amphitheater at Virginia Beach56 locals recommend
Lynnhaven Mall99 locals recommend
Mount Trashmore Park83 locals recommend
MacArthur Center154 locals recommend
The NorVa47 locals recommend
Greenbrier Mall25 locals recommend

Other great vacation rentals in Chesapeake

Superhost

Apartment in Portsmouth

4.84 out of 5 average rating, 285 reviews

Spacious 2 bedroom apt in Historic Port Norfolk

Aug 15 – 22

G$21,456 GYD per night
Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 280 reviews

Sun Sea and Sand

Aug 26 – Sep 2

G$28,189 GYD per night
Guest favorite

Place to stay in Virginia Beach

4.99 out of 5 average rating, 106 reviews

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

May 4 – 11

G$28,822 GYD per night
Guest favorite

Townhouse in Chesapeake

4.92 out of 5 average rating, 106 reviews

Tasha's Townhouse *King, Queen, Twin*

Aug 20 – 27

G$46,505 GYD per night
Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 239 reviews

Cozy Ground Floor Apt in Historic Home

Jan 16 – 23

G$21,438 GYD per night
Guest favorite

Home in Smithfield

4.96 out of 5 average rating, 198 reviews

Mason Manor - Downtown Smithfield next to WCP

Nov 28 – Dec 5

G$23,782 GYD per night
Guest favorite

Guest suite in Virginia Beach

4.85 out of 5 average rating, 348 reviews

Guest Suite Studio w/ Kitchenette & Private bath.

May 20 – 27

G$23,316 GYD per night
Guest favorite

Tiny home in Hampton

4.92 out of 5 average rating, 171 reviews

Hampton River Retreat Tiny House

Nov 9 – 16

G$26,536 GYD per night
Guest favorite

Guesthouse in Portsmouth

4.97 out of 5 average rating, 151 reviews

Spring Hill Guest Cottage - Portsmouth

Jan 29 – Feb 5

G$32,275 GYD per night
Guest favorite

Apartment in Chesapeake

5.0 out of 5 average rating, 25 reviews

Entire Apartment - No Cleaning Fees!

Oct 8 – 15

G$19,991 GYD per night
Guest favorite

Apartment in Chesapeake

4.95 out of 5 average rating, 39 reviews

Blissful Nook @ Washington

May 8 – 15

G$21,299 GYD per night
Guest favorite

Guest suite in Chesapeake

4.91 out of 5 average rating, 44 reviews

Guest Suite with Private entrance & bathroom

Jun 29 – Jul 6

G$19,668 GYD per night

Other great vacation rentals in Chesapeake

Guest favorite

Home in Chesapeake

4.91 out of 5 average rating, 33 reviews

Hidden Gem in Chesapeake, Virginia

Sep 28 – Oct 5

G$30,803 GYD per night
Guest favorite

Bungalow in Chesapeake

4.93 out of 5 average rating, 69 reviews

Private and Cozy Bungalow Loaded with Amenities

Apr 30 – May 7

G$23,876 GYD per night
Guest favorite

Townhouse in Chesapeake

4.82 out of 5 average rating, 28 reviews

Best Temporary Rental in Chesapeake

Jan 16 – 23

G$25,858 GYD per night
Guest favorite

Condo in Portsmouth

4.96 out of 5 average rating, 84 reviews

‘Captains Corner’ 1 Bedrm CONDO Historic Old Towne

Apr 22 – 29

G$21,318 GYD per night
Guest favorite

Guesthouse in Suffolk

4.9 out of 5 average rating, 50 reviews

The Magnolia Guesthouse With A Private Entrance

Sep 2 – 9

G$19,554 GYD per night
Guest favorite

Townhouse in Chesapeake

4.9 out of 5 average rating, 99 reviews

Family friendly townhouse

May 17 – 24

G$37,204 GYD per night
Guest favorite

Apartment in Suffolk

5.0 out of 5 average rating, 69 reviews

Country Living Guest House (Upstairs/Downstairs)

Mar 17 – 24

G$22,669 GYD per night
Superhost

Townhouse in Virginia Beach

4.84 out of 5 average rating, 76 reviews

3 bedroom townhome by Town Center

Feb 25 – Mar 4

G$19,838 GYD per night
Guest favorite

Home in Chesapeake

4.93 out of 5 average rating, 14 reviews

Modern Escape King Suite! 2 BDR

Dec 16 – 23

G$35,281 GYD per night
Superhost

Apartment in Chesapeake

4.84 out of 5 average rating, 25 reviews

2BR Self Check-in, Fast Wi-Fi

Apr 3 – 10

G$28,529 GYD per night
Superhost

Camper/RV in Chesapeake

4.84 out of 5 average rating, 85 reviews

Waterfront Airstream in peaceful central location!

May 12 – 19

G$15,953 GYD per night
Guest favorite

Home in Portsmouth

4.96 out of 5 average rating, 26 reviews

Penny’s Palace 1 Bed/1 Bath Home

Jun 9 – 14

G$22,996 GYD per night

Quick stats about vacation rentals in Chesapeake

Total rentals

1.1K properties

Rentals with dedicated workspaces

620 properties have a dedicated workspace

Rentals with a pool

140 properties have a pool

Pet-friendly rentals

370 properties allow pets

Family-friendly rentals

520 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 320 vacation rentals in Ghent, over 580 vacation rentals in Downtown Norfolk, over 580 vacation rentals in Olde Towne, 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 620 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 370 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 townhouse rentals in Chesapeake?

    Experience the best of Chesapeake with our townhouse rentals, starting at about $20 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 apartment rentals in Chesapeake have a gym?

    Absolutely! We offer over 80 apartment 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 170 house 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 310 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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