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
Flat in Chesapeake
5.0 out of 5 average rating, 29 reviewsEntire Apartment - No Cleaning Fees!
28 Oct – 4 Nov
Flat in Chesapeake
4.95 out of 5 average rating, 42 reviewsBlissful Nook @ Washington
3–10 Jul
Flat in Chesapeake
4.9 out of 5 average rating, 21 reviewsWarm Luxury unit Central Greenbrier
5–12 Mar
Flat in Chesapeake
4.97 out of 5 average rating, 97 reviews2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.
13–20 Jul
Flat in Chesapeake
4.89 out of 5 average rating, 9 reviewsSerene Tree House Retreat | Spacious 1br/1bth Home
25 Sep – 2 Oct
Flat in Chesapeake
4.94 out of 5 average rating, 17 reviewsCountry Escape - Next DOOR - Hidden Gem
10–17 Aug
Flat in Suffolk
4.97 out of 5 average rating, 29 reviewsOne Bedroom Loft in Bridgeport, North Suffolk, VA
23 Feb – 2 Mar
Flat in Portsmouth
4.96 out of 5 average rating, 69 reviews"The Ponderosa B" - Close to the Casino
26 Nov – 1 Dec
Private apartment rentals
Flat in Chesapeake
4.92 out of 5 average rating, 13 reviewsCharming efficiency!
5–12 Jul
Flat in Portsmouth
4.98 out of 5 average rating, 60 reviewsEnglish Basement Hide-Away
12–19 Oct
Flat in Hampton
4.97 out of 5 average rating, 66 reviewsPenthouse Paradise On The Harbor
3–10 Nov
Flat in Portsmouth
4.88 out of 5 average rating, 60 reviewsOld world charm
2–9 Jun
Flat in Norfolk
4.82 out of 5 average rating, 11 reviewsElite City Stay
6–13 Jan
Flat in Virginia Beach
4.95 out of 5 average rating, 59 reviewsNorth End Beach Cottage Apt - One Block from Beach
7–14 Dec
Flat in Portsmouth
4.8 out of 5 average rating, 44 reviewsCozy 2-bedroom unit in Port-Norfolk
3–10 Dec
Flat in Virginia Beach
4.87 out of 5 average rating, 15 reviewsNice Apartment Centrally Located
10–17 Mar
Apartment rentals with a hot tub
Flat in Virginia Beach
4.78 out of 5 average rating, 9 reviewsBarclay Towers Ocean Front 2, Virginia Beach
3–10 Aug
Flat in Virginia Beach
4.86 out of 5 average rating, 7 reviewsVirginia Beach Oceanfront Condo
15–22 Jun
Flat in Virginia Beach
5.0 out of 5 average rating, 13 reviewsBayside condo on the beach in Sandbridge
31 Mar – 7 Apr
Flat in Virginia Beach
4.73 out of 5 average rating, 15 reviewsSojourn Sanctuary Seaside Escape 3 BR
31 Mar – 7 Apr
Flat in Norfolk
5.0 out of 5 average rating, 5 reviewsFireplace W/Balcony 1-Min Walk Downtown Norfolk.
21–28 Jan
Flat in Williamsburg
5.0 out of 5 average rating, 3 reviewsKing’s Creek Resort. Next to Country Water 2BR/2BA
27 Jul – 3 Aug
Flat in Williamsburg
4.75 out of 5 average rating, 4 reviews*No Resort Fees Powhatan 4 bdrm
1–8 Jun
Flat in Williamsburg
5.0 out of 5 average rating, 10 reviewsColonial Experience: 2-BR in Williamsburg
1–8 May
Quick stats about flat 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
5.2T reviews
Nightly prices starting at
₹834 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
- Flat rentals United States
- Serviced apartment rentals United States
- Flat rentals Outer Banks
- Serviced apartment rentals Virginia Beach
- Flat rentals Virginia Beach
- Flat rentals Virginia
- Serviced apartment rentals Virginia
- Flat rentals Richmond
- Monthly Rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
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- Apartment rentals Chesapeake
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