House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Chesapeake
House rentals with a pool
Home in Gloucester Point
4.99 out of 5 average rating, 148 reviewsYork River Vacation Home
Home in Virginia Beach
4.83 out of 5 average rating, 107 reviewsStunning Views of Back Bay & Seconds to the Beach
Home in Virginia Beach
4.96 out of 5 average rating, 165 reviewsSalida del Sol, North End Beach
Home in Virginia Beach
4.88 out of 5 average rating, 116 reviewsHalf house w/pool & new patio all to yourself
Home in Norfolk
4.75 out of 5 average rating, 117 reviewsBEACH/ POOL HOUS, 1 min walk to the beach Norfolk
Home in Portsmouth
4.88 out of 5 average rating, 8 reviewsElegance Escape on Saunders Dr
Home in Virginia Beach
4.94 out of 5 average rating, 93 reviewsCountry Comfort Close to the Beaches
Home in Portsmouth
4.93 out of 5 average rating, 61 reviewsWooded Wonderland Miniature Golf Hot tub Pool
Weekly house rentals
Home in Hampton
4.94 out of 5 average rating, 124 reviews1950s bungalow, 2-1/2 blocks from Buckroe Beach
Home in Chesapeake
4.88 out of 5 average rating, 26 reviewsChesapeake. 3 Bedroom 1-1/2 Bath Small family home
Home in Chesapeake
4.98 out of 5 average rating, 53 reviewsCook's Country Escape - House nestled in woods
Home in Chesapeake
4.92 out of 5 average rating, 38 reviewsHidden Gem in Chesapeake, Virginia
Home in Hampton
4.93 out of 5 average rating, 14 reviewsTiny Blue Beach House
Home in Portsmouth
4.97 out of 5 average rating, 39 reviewsPenny’s Palace 1 Bed/1 Bath Home
Home in Gloucester Point
4.99 out of 5 average rating, 74 reviewsCharming coastal home w/ outdoor area and river views
Home in Chesapeake
5.0 out of 5 average rating, 10 reviewsBeautiful home in Chesapeake
Private house rentals
Home in Norfolk
4.92 out of 5 average rating, 59 reviewsTiny House Near Beach & Naval Base - Privacy Fence
Home in Chesapeake
5.0 out of 5 average rating, 34 reviewsSleeps 6-8, King bed, 2.5 baths
Home in Norfolk
4.92 out of 5 average rating, 53 reviewsBayview Beach/Airport/3 Bedrm/6 Beds/2 Bath/ 4TV
Home in Virginia Beach
4.79 out of 5 average rating, 14 reviewsCozy Townhome- central location
Home in Portsmouth
4.86 out of 5 average rating, 7 reviewsCozy Portsmouth Retreat 2BR/1BA
Home in Norfolk
4.93 out of 5 average rating, 68 reviewsStayHere - Norfolk
Home in Hampton
4.96 out of 5 average rating, 50 reviewsExclusive Beachfront Home w/ 180° Views & Hot Tub!
Home in Chesapeake
5.0 out of 5 average rating, 34 reviewsTownhome in Great Bridge Newly Renovated
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
Destinations to explore
- Outer Banks Holiday rentals
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