Holiday rentals in Chesapeake
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Top-rated holiday rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake holiday rentals
Other great holiday rentals in Chesapeake
Guest favourite
Flat in Chesapeake
5.0 out of 5 average rating, 29 reviewsEntire Apartment - No Cleaning Fees!
24–31 Jan
₹9,653 per night
Guest favourite
Flat in Chesapeake
4.95 out of 5 average rating, 42 reviewsBlissful Nook @ Washington
3–10 Jul
₹9,882 per night
Guest favourite
Home in Chesapeake
4.88 out of 5 average rating, 24 reviewsChesapeake. 3 Bedroom 1-1/2 Bath Small family home
3–10 Nov
₹8,592 per night
Guest favourite
Guest suite in Chesapeake
4.91 out of 5 average rating, 46 reviewsGuest Suite with Private entrance & bathroom
16–23 Jul
₹9,040 per night
Guest favourite
Townhouse in Chesapeake
4.97 out of 5 average rating, 29 reviewsCenter of Greenbrier
29 Aug – 5 Sep
₹11,718 per night
Guest favourite
Flat in Chesapeake
4.94 out of 5 average rating, 17 reviewsCountry Escape - Next DOOR - Hidden Gem
10–17 Aug
₹9,063 per night
Superhost
Townhouse in Virginia Beach
4.84 out of 5 average rating, 76 reviews3 bedroom townhome by Town Center
25 Feb – 4 Mar
₹8,041 per night
Superhost
Guest house in Suffolk
4.82 out of 5 average rating, 28 reviewsLakeside Retreat
17–24 May
₹9,412 per night
Quick stats about holiday rentals in Chesapeake
Total rentals
1.1T properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Rentals with a pool
150 properties have a pool
Pet-friendly rentals
340 properties allow pets
Family-friendly rentals
510 properties are a good fit for families
Total number of reviews
31T reviews
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 Chesapeake
- Rentals with a cinema Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with lake access Chesapeake
- Apartment rentals Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with a firepit Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with a patio Chesapeake
- Rentals with a hot tub Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with breakfast Chesapeake
- Private suite rentals Chesapeake
- Family-friendly rentals Chesapeake
- Monthly Rentals Chesapeake
- Rentals with a fireplace Chesapeake
- House rentals Chesapeake
- Waterfront rentals Chesapeake
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