Holiday rentals in Chesapeake

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Top-rated holiday rentals in Chesapeake

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

Guest favourite
Guest suite in Chesapeake
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!
19–26 Jun
₹7,803 per night
4.97 out of 5 average rating, 224 reviews
Guest favourite
Guest house in Norfolk
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.
19–26 Sep
₹9,306 per night
4.98 out of 5 average rating, 547 reviews
Guest favourite
Guest suite in Chesapeake
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.
30 Jan – 6 Feb
₹8,208 per night
4.95 out of 5 average rating, 465 reviews

Popular amenities for Chesapeake holiday 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 holiday rentals in Chesapeake

Guest favourite
Home in Virginia Beach
Quilted Quarters by the Bay with Private Entrance
30 Aug – 6 Sep
₹8,048 per night
4.89 out of 5 average rating, 199 reviews
Guest favourite
Flat in Chesapeake
Entire Apartment - No Cleaning Fees!
26 Feb – 5 Mar
₹9,035 per night
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Chesapeake
Warm Luxury unit Central Greenbrier
9–16 Sep
₹8,412 per night
4.89 out of 5 average rating, 18 reviews
Guest favourite
Townhouse in Chesapeake
Center of Greenbrier
17–24 May
₹10,070 per night
4.96 out of 5 average rating, 23 reviews
Guest favourite
Guest suite in Chesapeake
Guest Suite with Private entrance & bathroom
5–12 Jul
₹6,751 per night
4.91 out of 5 average rating, 45 reviews
Guest favourite
Flat in Chesapeake
Blissful Nook @ Washington
29 May – 5 Jun
₹7,696 per night
4.95 out of 5 average rating, 39 reviews
Guest favourite
Flat in Chesapeake
Country Escape - Next DOOR - Hidden Gem
10–17 Jun
₹5,910 per night
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Chesapeake
Chesapeake. 3 Bedroom 1-1/2 Bath Small family home
31 Dec – 7 Jan
₹7,404 per night
4.84 out of 5 average rating, 19 reviews
Guest favourite
Townhouse in Chesapeake
Family friendly townhouse
5–12 Apr
₹11,531 per night
4.9 out of 5 average rating, 99 reviews
Guest favourite
Home in Chesapeake
Hidden Gem in Chesapeake, Virginia
5–12 Oct
₹10,364 per night
4.94 out of 5 average rating, 32 reviews
Guest favourite
Flat in Portsmouth
The Bunny Trail - perfect for travel nurses!
21–28 Mar
₹4,962 per night
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Chesapeake
Modern Escape King Suite! 2 BDR
2–9 Jan
₹12,081 per night
4.92 out of 5 average rating, 13 reviews

Quick stats about holiday rentals in Chesapeake

Total rentals

1.1T 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

31T reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake