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 Sandbridge
4.99 out of 5 average rating, 69 reviewsThe Golden Hour - Let’s Make Some Memories
Home in Virginia Beach
4.82 out of 5 average rating, 112 reviewsTHE OLD BEACON 1 | Beach Living
Home in Virginia Beach
5 out of 5 average rating, 30 reviewsPaint The Beach Pink! Full House | Gas Fire Pit
Home in Virginia Beach
4.94 out of 5 average rating, 106 reviewsCountry Comfort Close to the Beaches
Home in Norfolk
4.95 out of 5 average rating, 81 reviewsGorgeous Vacation House
Home in Sandbridge
4.85 out of 5 average rating, 118 reviewsStunning Views of Back Bay & Seconds to the Beach
Home in Sandbridge
4.79 out of 5 average rating, 43 reviews5BR Waterfront 350ft-Beach Salt Pool Reno 14 guest
Home in Hampton
4.92 out of 5 average rating, 88 reviews4BD home w/ game room & pool near Langley & PTC!
Weekly house rentals
Home in Chic's Beach
4.96 out of 5 average rating, 127 reviewsWater Oaks at Chic's Beach
Home in Norfolk
4.87 out of 5 average rating, 69 reviewsLove this Spacious ranch house near Beach & Base
Home in Virginia Beach
4.88 out of 5 average rating, 64 reviewsAt Oceanside on the gold coast in the North End!
Home in Virginia Beach
4.71 out of 5 average rating, 337 reviewsCottage 2 Blocks to Virginia Beach Oceanfront -III
Home in East Ocean View
4.93 out of 5 average rating, 178 reviews@Whit’s End? Come in and Relax
Home in Sandbridge
4.99 out of 5 average rating, 77 reviewsBreathtaking Ocean views at Pinch Me, 8bdrm, 6bath
Home in Virginia Beach
4.95 out of 5 average rating, 37 reviewsFamily Retreat | Crib | Minutes to Beach & Town
Home in Virginia Beach
4.88 out of 5 average rating, 137 reviewsRanch home with open floor plan
Private house rentals
Home in Norfolk
4.81 out of 5 average rating, 47 reviewsLittle Bay Getaway w/private pier
Home in East Ocean View
4.92 out of 5 average rating, 327 reviewsNew Beach Home on the Chesapeake Bay
Home in Newport News
4.89 out of 5 average rating, 140 reviewsFamily Haven Retreat by CNU| 1st FL master
Home in Virginia Beach
5 out of 5 average rating, 57 reviews*NEW* Spacious/Standalone 4BR Beach House
Home in Chesapeake
4.78 out of 5 average rating, 73 reviewsThe Full House
Home in Buckroe Beach
4.95 out of 5 average rating, 111 reviewsQuaint and Comfortable Buckroe Beach Getaway.
Home in Virginia Beach
4.87 out of 5 average rating, 174 reviewsThe Stunning Sandpiper!!
Home in Hampton
4.97 out of 5 average rating, 37 reviewsQuiet, Quaint, Cozy, Cul-de-sac, Hottub & GYM/YOGA
Quick stats about house rentals in Chesapeake
Total rentals
570 properties
Total number of reviews
14K reviews
Family-friendly rentals
280 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
320 properties have a dedicated workspace
Destinations to explore
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- Rentals with pools Chesapeake
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