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 Virginia Beach
4.93 out of 5 average rating, 118 reviewsWalk to the Beach from Pretty Inn Pink
Aug 2 – 9
Apartment in Chesapeake
4.9 out of 5 average rating, 21 reviewsWarm Luxury unit Central Greenbrier
Jan 14 – 21
Apartment in Chesapeake
4.95 out of 5 average rating, 42 reviewsBlissful Nook @ Washington
Aug 6 – 13
Apartment in Chesapeake
4.9 out of 5 average rating, 10 reviewsSerene Tree House Retreat | Spacious 1br/1bth Home
Mar 26 – Apr 2
Apartment in Chesapeake
5.0 out of 5 average rating, 30 reviewsEntire Apartment - No Cleaning Fees!
Feb 2 – 9
Apartment in Chesapeake
4.97 out of 5 average rating, 97 reviews2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.
Jul 21 – 28
Apartment in Chesapeake
4.94 out of 5 average rating, 18 reviewsCountry Escape - Next DOOR - Hidden Gem
Feb 16 – 23
Apartment in Virginia Beach
4.85 out of 5 average rating, 33 reviewsThe Lodge! 1BR Studio with private entrance.
Apr 3 – 10
Private apartment rentals
Apartment in Chesapeake
4.92 out of 5 average rating, 13 reviewsCharming efficiency!
May 25 – Jun 1
Apartment in Portsmouth
4.96 out of 5 average rating, 71 reviews"The Ponderosa B" - Close to the Casino
Feb 1 – 8
Apartment in Portsmouth
4.94 out of 5 average rating, 71 reviewsCharming cozy apt historic in Old Towne Portsmouth
Feb 22 – Mar 1
Apartment in Portsmouth
4.98 out of 5 average rating, 60 reviewsEnglish Basement Hide-Away
Jul 23 – 30
Apartment in Norfolk
4.82 out of 5 average rating, 11 reviewsElite City Stay
Jan 17 – 24
Apartment in Portsmouth
4.89 out of 5 average rating, 61 reviewsOld world charm
Jun 9 – 16
Apartment in Norfolk
4.94 out of 5 average rating, 78 reviewsClose 2 East Beach, EOV, King Bed, Top Floor
May 12 – 17
Apartment in Virginia Beach
4.95 out of 5 average rating, 59 reviewsNorth End Beach Cottage Apt - One Block from Beach
Nov 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
Feb 17 – 24
Apartment in Virginia Beach
4.73 out of 5 average rating, 15 reviewsSojourn Sanctuary Seaside Escape 3 BR
Dec 29 – Jan 5
Apartment in Williamsburg
5.0 out of 5 average rating, 10 reviewsColonial Experience: 2-BR in Williamsburg
May 8 – 15
Apartment in Williamsburg
4.6 out of 5 average rating, 5 reviews*No Resort Fees Powhatan 4 bdrm
Jul 8 – 15
Apartment in Williamsburg
4.6 out of 5 average rating, 5 reviewsWilliamsburg 4 Bedroom Suite!
Jul 9 – 16
Apartment in Norfolk
5.0 out of 5 average rating, 5 reviewsFireplace W/Balcony 1-Min Walk Downtown Norfolk.
Mar 9 – 16
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
$10 before taxes and fees
Destinations to explore
- Outer Banks Vacation rentals
- Virginia Beach Vacation rentals
- Richmond Vacation rentals
- Norfolk Vacation rentals
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- Rentals with pools Chesapeake
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