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 Virginia Beach
4.96 out of 5 average rating, 163 reviewsSalida del Sol, North End Beach
9–16 Oct
Home in Virginia Beach
4.83 out of 5 average rating, 106 reviewsStunning Views of Back Bay & Seconds to the Beach
12–19 Sept
Home in Norfolk
4.75 out of 5 average rating, 117 reviewsBEACH/ POOL HOUS, 1 min walk to the beach Norfolk
24 Jun – 1 Jul
Home in Portsmouth
4.83 out of 5 average rating, 6 reviewsElegance Escape on Saunders Dr
19–26 Dec
Home in Virginia Beach
4.94 out of 5 average rating, 93 reviewsCountry Comfort Close to the Beaches
6–13 Jan
Home in Portsmouth
4.93 out of 5 average rating, 58 reviewsWooded Wonderland Miniature Golf Hot tub Pool
9–16 Feb
Home in Norfolk
4.96 out of 5 average rating, 27 reviewsThe Seaglass Cottage
27 Sept – 4 Oct
Home in Suffolk
4.8 out of 5 average rating, 61 reviewsPerfect Getaway!
4–11 Oct
Weekly house rentals
Home in Chesapeake
4.94 out of 5 average rating, 17 reviewsModern Escape King Suite! 2 BDR
12–19 Nov
Home in Chesapeake
4.92 out of 5 average rating, 38 reviewsHidden Gem in Chesapeake, Virginia
24 Nov – 1 Dec
Home in Chesapeake
4.78 out of 5 average rating, 27 reviewsExperience Chesapeake Your Way and Relax with Golf
14–21 Nov
Home in Chesapeake
4.98 out of 5 average rating, 52 reviewsCook's Country Escape - House nestled in woods
3–10 Dec
Home in Norfolk
4.86 out of 5 average rating, 7 reviewsBeach Cottage #5 at OceanView
11–18 Dec
Home in Chesapeake
5.0 out of 5 average rating, 33 reviewsSleeps 6-8, King bed, 2.5 baths
27 Jul – 3 Aug
Home in Portsmouth
4.92 out of 5 average rating, 39 reviewsHidden Gem
17–24 Jul
Home in Chesapeake
4.96 out of 5 average rating, 25 reviewsThe Sparks Home- w/ Lux Kitchen
27 Dec – 3 Jan
Private house rentals
Home in Norfolk
4.92 out of 5 average rating, 51 reviewsBayview Beach/Airport/3 Bedrm/6 Beds/2 Bath/ 4TV
20–27 Sept
Home in Chesapeake
4.91 out of 5 average rating, 32 reviewsThe Bird’s Nest
4–11 Mar
Home in Norfolk
4.96 out of 5 average rating, 69 reviewsThe OV Beach Shack : cozy, fun beach house!
28 Apr – 5 May
Home in Knotts Island
4.94 out of 5 average rating, 83 reviewsIsland Lotus Yoga & Spa
11–18 Oct
Home in Virginia Beach
5.0 out of 5 average rating, 3 reviewsPerfect for 2! Walk to Beach #2
4–11 Jan
Home in Hampton
4.95 out of 5 average rating, 21 reviewsTiny Home In Buckroe Beach
3–10 Oct
Home in Suffolk
4.8 out of 5 average rating, 20 reviewsLUXE Railroad Villa
8–15 Feb
Home in Virginia Beach
4.83 out of 5 average rating, 6 reviewsParadise On Pacific
26 Jan – 2 Feb
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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