Apartment holiday 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.
Holiday rentals for every style
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Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals
Apartment in Virginia Beach
4.91 out of 5 average rating, 116 reviewsWalk to beach BEAUTIFUL 2BR 1BA condo
30 Oct – 6 Nov
Apartment in Virginia Beach
4.84 out of 5 average rating, 237 reviewsBeautiful Beachfront Condo
3–10 Oct
Apartment in Virginia Beach
4.79 out of 5 average rating, 120 reviewsBeach Bliss Oasis
29 Dec – 5 Jan
Apartment in Virginia Beach
4.8 out of 5 average rating, 163 reviewsRetreat By the Sea Full Kitchen 1 St. to the Ocean
1–8 Oct
Apartment in Williamsburg
4.81 out of 5 average rating, 100 reviewsBook a Piece of History at Kingsmill Williamsburg
5–12 Jul
Apartment in Williamsburg
4.96 out of 5 average rating, 51 reviewsComfy 1BR w pond view Kingsmill
22–29 Aug
Apartment in Portsmouth
4.97 out of 5 average rating, 88 reviews‘Captains Corner’ 1 Bedrm CONDO Historic Old Towne
14–21 Oct
Apartment in Virginia Beach
4.85 out of 5 average rating, 92 reviewsBeach Bungalow on the Boardwalk
21–28 Oct
Pet-friendly apartment rentals
Apartment in Chesapeake
5.0 out of 5 average rating, 5 reviews2BR Condo in Chesapeake - Western Branch
15–22 Jul
Apartment in Norfolk
4.98 out of 5 average rating, 60 reviewsBeachfront Getaway, Pet Friendly, Mermaid Suite
20–27 Aug
Apartment in Moyock
5.0 out of 5 average rating, 13 reviewsBrand New Townhome - Family and Dog Friendly
9–16 Jan
Apartment in Norfolk
5.0 out of 5 average rating, 22 reviewsBeachfront Condo; Amazing views (1 bedrm, 1 bath)
9–16 Mar
Apartment in Williamsburg
4.97 out of 5 average rating, 75 reviewsLovely large 2/2 bath, water views in Kingsmill
21–28 Oct
Apartment in Norfolk
4.85 out of 5 average rating, 48 reviewslovely condo near chesapeake bay
16–23 Jul
Apartment in Hampton
4.9 out of 5 average rating, 72 reviewsCozy & Fun Hampton Condo- WIFI & W/D!
23–30 Apr
Apartment in Virginia Beach
4.89 out of 5 average rating, 235 reviewsCoastal Coral - Oceanfront
3–10 May
Apartment rentals with a pool
Apartment in Virginia Beach
4.98 out of 5 average rating, 54 reviews2BD/2BR Beachfront Condo Near Wildlife Refuge
1–8 Oct
Apartment in Virginia Beach
4.92 out of 5 average rating, 66 reviewsOceanfront/Boardwalk Complex, Beach, Pool, Balcony
11–18 Dec
Apartment in Virginia Beach
4.97 out of 5 average rating, 60 reviewsParadise at the Beach
2–9 Jun
Apartment in Virginia Beach
4.86 out of 5 average rating, 36 reviewsOcean front best beach, boardwalk, dolphins!
28 Mar – 4 Apr
Apartment in Virginia Beach
5.0 out of 5 average rating, 3 reviewsSojourn | Southern Dunes | Sleeps 6
14–21 Sep
Apartment in Virginia Beach
4.89 out of 5 average rating, 35 reviewsVA Beach Retreat! Quiet and perfect for families!
28 Nov – 5 Dec
Apartment in Virginia Beach
4.89 out of 5 average rating, 57 reviews❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
21–28 Sep
Apartment in Williamsburg
4.71 out of 5 average rating, 14 reviewsTimeshare Resort condo- 1 bdrm
27 May – 3 Jun
Quick stats about apartment rentals in Chesapeake
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1T reviews
Nightly prices starting at
₹4,170 before taxes and fees
Destinations to explore
- Outer Banks Holiday rentals
- Virginia Beach Holiday rentals
- Richmond Holiday rentals
- Norfolk Holiday rentals
- Williamsburg Holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- Apartment rentals Outer Banks
- Apartment rentals Virginia Beach
- Beach apartment rentals Virginia Beach
- Apartment rentals Virginia
- Apartment rentals Richmond
- Family-friendly rentals Chesapeake
- House rentals Chesapeake
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- Waterfront rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a cinema Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Private suite rentals Chesapeake
- Rentals with a firepit Chesapeake
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- Monthly Rentals Chesapeake
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- Townhouse rentals Chesapeake
- Flat rentals Chesapeake
- Rentals with lake access Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with pools Chesapeake
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