Apartment vacation rentals in Chesapeake
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Top-rated apartment rentals in Chesapeake
Guests agree: these apartments 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 apartment rentals
Weekly apartment rentals
Apartment in Chesapeake
4.95 out of 5 average rating, 42 reviewsBlissful Nook @ Washington
Jul 3 – 10
Apartment in Chesapeake
5.0 out of 5 average rating, 30 reviewsEntire Apartment - No Cleaning Fees!
Jan 2 – 9
Apartment in Chesapeake
4.9 out of 5 average rating, 21 reviewsWarm Luxury unit Central Greenbrier
Oct 12 – 19
Apartment in Chesapeake
4.94 out of 5 average rating, 17 reviewsCountry Escape - Next DOOR - Hidden Gem
Aug 4 – 11
Apartment in Chesapeake
4.89 out of 5 average rating, 9 reviewsSerene Tree House Retreat | Spacious 1br/1bth Home
Jan 5 – 12
Apartment in Chesapeake
4.97 out of 5 average rating, 73 reviews1 King Master BR. ⚡️Fast Wifi. 🔐 Easy Self Check In
Jun 10 – 17
Apartment in Portsmouth
4.96 out of 5 average rating, 71 reviews"The Ponderosa B" - Close to the Casino
Oct 18 – 23
Apartment in Virginia Beach
4.85 out of 5 average rating, 33 reviewsThe Lodge! 1BR Studio with private entrance.
Jan 20 – 27
Private apartment rentals
Apartment in Portsmouth
4.94 out of 5 average rating, 71 reviewsCharming cozy apt historic in Old Towne Portsmouth
Sep 16 – 23
Apartment in Portsmouth
4.98 out of 5 average rating, 60 reviewsEnglish Basement Hide-Away
Nov 4 – 11
Apartment in Hampton
4.97 out of 5 average rating, 67 reviewsPenthouse Paradise On The Harbor
Feb 1 – 8
Apartment in Norfolk
4.82 out of 5 average rating, 11 reviewsElite City Stay
Jan 6 – 13
Apartment in Portsmouth
4.89 out of 5 average rating, 61 reviewsOld world charm
Oct 11 – 18
Apartment in Virginia Beach
4.95 out of 5 average rating, 59 reviewsNorth End Beach Cottage Apt - One Block from Beach
Mar 8 – 15
Apartment in Portsmouth
4.8 out of 5 average rating, 44 reviewsCozy 2-bedroom unit in Port-Norfolk
Dec 3 – 10
Apartment in Virginia Beach
4.88 out of 5 average rating, 16 reviewsNice Apartment Centrally Located
Dec 22 – 29
Apartment rentals with a hot tub
Apartment in Virginia Beach
4.86 out of 5 average rating, 7 reviewsVirginia Beach Oceanfront Condo
Jun 15 – 22
Apartment in Virginia Beach
4.78 out of 5 average rating, 9 reviewsBarclay Towers Ocean Front 2, Virginia Beach
Aug 3 – 10
Apartment in Virginia Beach
5.0 out of 5 average rating, 13 reviewsBayside condo on the beach in Sandbridge
Dec 26 – Jan 2
Apartment in Virginia Beach
4.73 out of 5 average rating, 15 reviewsSojourn Sanctuary Seaside Escape 3 BR
Oct 9 – 16
Apartment in Norfolk
5.0 out of 5 average rating, 5 reviewsFireplace W/Balcony 1-Min Walk Downtown Norfolk.
Jan 3 – 10
Apartment in Williamsburg
5.0 out of 5 average rating, 10 reviewsColonial Experience: 2-BR in Williamsburg
May 3 – 10
Apartment in Williamsburg
4.6 out of 5 average rating, 5 reviews*No Resort Fees Powhatan 4 bdrm
Jun 1 – 8
Apartment in Williamsburg
4.6 out of 5 average rating, 5 reviewsWilliamsburg 4 Bedroom Suite!
Jun 18 – 25
Quick stats about apartment rentals in Chesapeake
Total rentals
220 properties
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
5.2K reviews
Nightly prices starting at
G$2,091 GYD before taxes and fees
Destinations to explore
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- Rentals with outdoor seating Chesapeake
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