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
Destinations to explore
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- Rentals with a fire pit Chesapeake
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