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, 163 reviewsSalida del Sol, North End Beach
Jan. 11 – 18
Home in Virginia Beach
4.83 out of 5 average rating, 105 reviewsStunning Views of Back Bay & Seconds to the Beach
Feb. 24 – Mar. 3
Home in Norfolk
4.75 out of 5 average rating, 117 reviewsBEACH/ POOL HOUS, 1 min walk to the beach Norfolk
Sep. 7 – 14
Home in Virginia Beach
4.88 out of 5 average rating, 115 reviewsHalf house w/pool & new patio all to yourself
Jun. 16 – 23
Home in Portsmouth
4.83 out of 5 average rating, 6 reviewsElegance Escape on Saunders Dr
Dec. 11 – 18
Home in Virginia Beach
4.93 out of 5 average rating, 92 reviewsCountry Comfort Close to the Beaches
Apr. 5 – 12
Home in Portsmouth
4.93 out of 5 average rating, 57 reviewsWooded Wonderland Miniature Golf Hot tub Pool
Oct. 10 – 17
Home in Norfolk
4.96 out of 5 average rating, 25 reviewsThe Seaglass Cottage
Mar. 18 – 25
Weekly house rentals
Home in Chesapeake
4.98 out of 5 average rating, 52 reviewsCook's Country Escape - House nestled in woods
Feb. 17 – 24
Home in Chesapeake
4.92 out of 5 average rating, 38 reviewsHidden Gem in Chesapeake, Virginia
Dec. 12 – 19
Home in Chesapeake
4.94 out of 5 average rating, 17 reviewsModern Escape King Suite! 2 BDR
Sep. 22 – 29
Home in Hampton
4.92 out of 5 average rating, 13 reviewsTiny Blue Beach House
Dec. 10 – 17
Home in Portsmouth
4.92 out of 5 average rating, 37 reviewsHidden Gem
Jul. 18 – 25
Home in Chesapeake
5.0 out of 5 average rating, 6 reviewsBeautiful home in Chesapeake
Oct. 8 – 15
Home in Chesapeake
5.0 out of 5 average rating, 33 reviewsSleeps 6-8, King bed, 2.5 baths
Jul. 8 – 15
Home in Portsmouth
4.97 out of 5 average rating, 36 reviewsPenny’s Palace 1 Bed/1 Bath Home
Aug. 18 – 25
Private house rentals
Home in Norfolk
4.92 out of 5 average rating, 50 reviewsBayview Beach/Airport/3 Bedrm/6 Beds/2 Bath/ 4TV
Oct. 17 – 24
Home in Hampton
4.95 out of 5 average rating, 19 reviewsTiny Home In Buckroe Beach
Apr. 6 – 13
Home in Norfolk
5.0 out of 5 average rating, 9 reviews2 Bedroom Apartment in Ocean View
May 25 – Jun. 1
Home in Chesapeake
5.0 out of 5 average rating, 5 reviewsRelaxing LRG 4BR near VA Beach/Ches, King! Arcade!
Jul. 8 – 15
Home in Knotts Island
4.94 out of 5 average rating, 83 reviewsIsland Lotus Yoga & Spa
Feb. 5 – 12
Home in Newport News
4.93 out of 5 average rating, 45 reviews1-Bedroom Home Near Christopher Newport University
Dec. 3 – 10
Home in Portsmouth
4.92 out of 5 average rating, 26 reviewsComfortable & Private 2 Bedrm Cottage w/ King bed.
Sep. 27 – Oct. 4
Home in Chesapeake
5.0 out of 5 average rating, 34 reviewsTownhome in Great Bridge Newly Renovated
Sep. 18 – 25
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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- Rentals with a firepit Chesapeake
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