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
Get the amount of space that is right for you
Popular amenities for house rentals in Chesapeake
House rentals with a pool
Home in Virginia Beach
4.96 out of 5 average rating, 161 reviewsSalida del Sol, North End Beach
11–18 Jan
Home in Gloucester Point
4.99 out of 5 average rating, 146 reviewsYork River Vacation Home
30 Jan – 6 Feb
Home in Virginia Beach
4.83 out of 5 average rating, 105 reviewsStunning Views of Back Bay & Seconds to the Beach
26 Oct – 2 Nov
Home in Norfolk
4.75 out of 5 average rating, 117 reviewsBEACH/ POOL HOUS, 1 min walk to the beach Norfolk
2–9 Sep
Home in Virginia Beach
4.93 out of 5 average rating, 92 reviewsCountry Comfort Close to the Beaches
16–23 Dec
Home in Portsmouth
4.93 out of 5 average rating, 56 reviewsWooded Wonderland Miniature Golf Hot tub Pool
26 Jan – 2 Feb
Home in Suffolk
4.8 out of 5 average rating, 61 reviewsPerfect Getaway!
5–12 Dec
Home in Norfolk
4.96 out of 5 average rating, 24 reviewsThe Seaglass Cottage
3–10 Mar
Weekly house rentals
Home in Virginia Beach
4.99 out of 5 average rating, 164 reviewsPlay by the bay beach house,
4–11 Feb
Home in Chesapeake
4.88 out of 5 average rating, 24 reviewsChesapeake. 3 Bedroom 1-1/2 Bath Small family home
13–20 Oct
Home in Chesapeake
4.98 out of 5 average rating, 51 reviewsCook's Country Escape - House nestled in woods
19–26 Jan
Home in Chesapeake
4.92 out of 5 average rating, 38 reviewsHidden Gem in Chesapeake, Virginia
22–29 Mar
Home in Hampton
4.92 out of 5 average rating, 12 reviewsTiny Blue Beach House
8–15 Dec
Home in Norfolk
5.0 out of 5 average rating, 3 reviewsBeach oasis
1–8 Aug
Home in Chesapeake
4.93 out of 5 average rating, 15 reviewsModern Escape King Suite! 2 BDR
5–12 Aug
Home in Portsmouth
4.92 out of 5 average rating, 37 reviewsHidden Gem
16–23 Jul
Private house rentals
Home in Norfolk
4.92 out of 5 average rating, 50 reviewsBayview Beach/Airport/3 Bedrm/6 Beds/2 Bath/ 4TV
22–29 Sep
Home in Portsmouth
4.97 out of 5 average rating, 36 reviewsPenny’s Palace 1 Bed/1 Bath Home
22–29 Sep
Home in Gloucester Point
4.99 out of 5 average rating, 69 reviewsCharming coastal home w/ outdoor area and river views
12–19 Nov
Home in Hampton
4.95 out of 5 average rating, 19 reviewsTiny Home In Buckroe Beach
23–30 Jan
Home in Virginia Beach
4.8 out of 5 average rating, 10 reviewsCozy Townhome- central location
19–24 Jul
Home in Virginia Beach
4.93 out of 5 average rating, 55 reviewsBeach Cottage #4 on 19th - 3 Blocks From Beach
20–27 Feb
Home in Chesapeake
4.96 out of 5 average rating, 24 reviewsThe Sparks Home- w/ Lux Kitchen
20–27 Jul
Home in Knotts Island
4.94 out of 5 average rating, 83 reviewsIsland Lotus Yoga & Spa
24–31 Oct
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
12T reviews
Destinations to explore
- Outer Banks Holiday rentals
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