Apartment holiday rentals in Chesapeake
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Top-rated apartment rentals in Chesapeake
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Holiday rentals for every style
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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
16 – 23 Sept
Apartment in Chesapeake
4.9 out of 5 average rating, 21 reviewsWarm Luxury unit Central Greenbrier
19 – 26 Jan
Apartment in Chesapeake
4.95 out of 5 average rating, 42 reviewsBlissful Nook @ Washington
30 July – 6 Aug
Apartment in Chesapeake
5.0 out of 5 average rating, 30 reviewsEntire Apartment - No Cleaning Fees!
12 – 19 Dec
Apartment in Chesapeake
4.9 out of 5 average rating, 10 reviewsSerene Tree House Retreat | Spacious 1br/1bth Home
9 – 16 Dec
Apartment in Chesapeake
4.97 out of 5 average rating, 97 reviews2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.
21 – 28 July
Apartment in Chesapeake
4.94 out of 5 average rating, 17 reviewsCountry Escape - Next DOOR - Hidden Gem
23 – 30 Oct
Apartment in Virginia Beach
4.85 out of 5 average rating, 33 reviewsThe Lodge! 1BR Studio with private entrance.
31 Mar – 7 Apr
Private apartment rentals
Apartment in Chesapeake
4.92 out of 5 average rating, 13 reviewsCharming efficiency!
30 June – 7 July
Apartment in Portsmouth
4.96 out of 5 average rating, 71 reviews"The Ponderosa B" - Close to the Casino
6 – 13 Dec
Apartment in Portsmouth
4.98 out of 5 average rating, 60 reviewsEnglish Basement Hide-Away
27 Aug – 3 Sept
Apartment in Hampton
4.97 out of 5 average rating, 69 reviewsPenthouse Paradise On The Harbor
9 – 16 Mar
Apartment in Virginia Beach
4.88 out of 5 average rating, 16 reviewsNice Apartment Centrally Located
17 – 24 Apr
Apartment in Portsmouth
4.89 out of 5 average rating, 61 reviewsOld world charm
6 – 13 Aug
Apartment in Hampton
5.0 out of 5 average rating, 9 reviewsCity Bliss: Stylish 1BR Escape
10 – 17 June
Apartment in Virginia Beach
4.95 out of 5 average rating, 59 reviewsNorth End Beach Cottage Apt - One Block from Beach
15 – 22 Apr
Apartment rentals with a hot tub
Apartment in Virginia Beach
4.86 out of 5 average rating, 7 reviewsVirginia Beach Oceanfront Condo
15 – 22 June
Apartment in Virginia Beach
4.78 out of 5 average rating, 9 reviewsBarclay Towers Ocean Front 2, Virginia Beach
3 – 10 Aug
Apartment in Virginia Beach
5.0 out of 5 average rating, 13 reviewsBayside condo on the beach in Sandbridge
12 – 19 Dec
Apartment in Virginia Beach
4.73 out of 5 average rating, 15 reviewsSojourn Sanctuary Seaside Escape 3 BR
1 – 8 Apr
Apartment in Williamsburg
5.0 out of 5 average rating, 6 reviewsSun-Drenched Williamsburg 2-BDR Hideaway.
8 – 15 May
Apartment in Williamsburg
4.6 out of 5 average rating, 5 reviews*No Resort Fees Powhatan 4 bdrm
8 – 15 July
Apartment in Williamsburg
4.6 out of 5 average rating, 5 reviewsWilliamsburg 4 Bedroom Suite!
29 May – 5 June
Apartment in Norfolk
5.0 out of 5 average rating, 5 reviewsFireplace W/Balcony 1-Min Walk Downtown Norfolk.
24 Feb – 3 Mar
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
$15 AUD before taxes and fees
Destinations to explore
- Outer Banks Accommodation & holiday rentals
- Virginia Beach Holiday rentals
- Richmond Accommodation & holiday rentals
- Norfolk Holiday rentals
- Williamsburg Accommodation & holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Accommodation & holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
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- Jersey City Holiday rentals
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- Serviced apartment rentals United States
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