House vacation rentals in Chesapeake
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Top-rated house rentals in Chesapeake
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake house rentals
House rentals with a pool
Home in Virginia Beach
4.96 out of 5 average rating, 168 reviewsSalida del Sol, North End Beach
Home in Gloucester Point
4.99 out of 5 average rating, 151 reviewsYork River Vacation Home
Home in Norfolk
4.75 out of 5 average rating, 118 reviewsBEACH/ POOL HOUS, 1 min walk to the beach Norfolk
Home in Sandbridge
4.83 out of 5 average rating, 108 reviewsStunning Views of Back Bay & Seconds to the Beach
Home in Virginia Beach
4.94 out of 5 average rating, 93 reviewsCountry Comfort Close to the Beaches
Home in Virginia Beach
4.94 out of 5 average rating, 16 reviews4BR House w 2 King BEDS,2 kitchens, POOL & SAUNA
Home in East Ocean View
4.97 out of 5 average rating, 30 reviewsThe Seaglass Cottage
Home in Portsmouth
4.93 out of 5 average rating, 67 reviewsWooded Wonderland Miniature Golf Hot tub Pool
Weekly house rentals
Home in Virginia Beach
4.85 out of 5 average rating, 154 reviewsThe Magnificent Meadowlark!
Home in Virginia Beach
4.84 out of 5 average rating, 208 reviewsHome Away from Home! A+Location, Clean, Great Yard
Home in Buckroe Beach
4.94 out of 5 average rating, 127 reviews1950s bungalow, 2-1/2 blocks from Buckroe Beach
Home in Virginia Beach
4.99 out of 5 average rating, 169 reviewsPlay by the bay beach house,
Home in Chesapeake
4.86 out of 5 average rating, 29 reviewsChesapeake. 3 Bedroom 1-1/2 Bath Small family home
Home in Chesapeake
4.98 out of 5 average rating, 57 reviewsCook's Country Escape - House nestled in woods
Home in Chesapeake
4.93 out of 5 average rating, 40 reviewsHidden Gem in Chesapeake, Virginia
Home in Norfolk
5 out of 5 average rating, 3 reviewsCozy and Convenient 2BR/2BA Near Downtown Norfolk
Private house rentals
Home in Gloucester Point
4.97 out of 5 average rating, 79 reviewsCharming coastal home w/ outdoor area and river views
Home in Virginia Beach
4.93 out of 5 average rating, 15 reviewsParadise On Pacific
Home in Chesapeake
5 out of 5 average rating, 37 reviewsSleeps 6-8, King bed, 2.5 baths
Home in Chesapeake
5 out of 5 average rating, 12 reviewsBeautiful home in Chesapeake
Home in Portsmouth
4.93 out of 5 average rating, 44 reviewsHidden Gem
Home in Chesapeake
4.95 out of 5 average rating, 20 reviewsModern Escape King Suite! 2 BDR
Home in East Ocean View
4.96 out of 5 average rating, 73 reviewsThe OV Beach Shack : cozy, fun beach house!
Home in Knotts Island
4.94 out of 5 average rating, 88 reviewsIsland Lotus Yoga & Spa
Quick stats about house rentals in Chesapeake
Total rentals
560 properties
Rentals with dedicated workspaces
320 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
160 properties allow pets
Family-friendly rentals
290 properties are a good fit for families
Total number of reviews
12K reviews
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