Vacation 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!
29 July – 5 Aug
4.97 out of 5 average rating, 224 reviews
Guest favourite
Cottage in Norfolk
Beautiful Cottage Waterfront Near Downtown Norfolk
A Beautiful Secluded Paradise! We respond quickly! This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer
26 May – 2 June
5.0 out of 5 average rating, 248 reviews
Guest favourite
Guesthouse 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.
2 – 9 Nov
4.98 out of 5 average rating, 547 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
Apartment in Portsmouth
Cozy Ground Floor Apt in Historic Home
13 – 20 Dec
4.96 out of 5 average rating, 238 reviews
Guest favourite
Home in Norfolk
Private Pool 🏊‍♂️ Hot Tub, Fire Pit🔥 Close to Beach 🐠
16 – 23 Jan
4.94 out of 5 average rating, 124 reviews
Superhost
Home in Virginia Beach
Chicks Beachfront
20 – 27 Nov
4.86 out of 5 average rating, 202 reviews
Guest favourite
Apartment in Chesapeake
Entire Apartment - No Cleaning Fees!
26 Sept – 3 Oct
5.0 out of 5 average rating, 24 reviews
Guest favourite
Apartment in Chesapeake
Warm Luxury unit Central Greenbrier
17 – 24 Oct
4.89 out of 5 average rating, 18 reviews
Guest favourite
Guest suite in Chesapeake
Guest Suite with Private entrance & bathroom
29 May – 5 June
4.91 out of 5 average rating, 45 reviews
Guest favourite
Apartment in Chesapeake
Country Escape - Next DOOR - Hidden Gem
10 – 17 June
4.92 out of 5 average rating, 13 reviews
Guest favourite
Townhouse in Chesapeake
Center of Greenbrier
24 – 31 Aug
4.96 out of 5 average rating, 23 reviews
Guest favourite
Home in Chesapeake
Chesapeake. 3 Bedroom 1-1/2 Bath Small family home
27 Feb – 6 Mar
4.84 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Chesapeake
Blissful Nook @ Washington
29 May – 5 June
4.95 out of 5 average rating, 39 reviews
Guest favourite
Guesthouse in Chesapeake
Peaceful, Private Studio Apartment!
22 – 29 June
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Chesapeake
The Sparks Home- w/ Lux Kitchen
22 – 29 Dec
4.95 out of 5 average rating, 20 reviews

Quick stats about holiday 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

Destinations to explore

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