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 Williamsburg
4.84 out of 5 average rating, 360 reviewsThe Nook
2–9 Jan
€ 112 per night
Guest favourite
Guest house in Yorktown
4.97 out of 5 average rating, 202 reviewsCharming Yorktown Battlefield Cottage
8–15 Jul
€ 120 per night
Guest favourite
Flat in Chesapeake
5.0 out of 5 average rating, 29 reviewsEntire Apartment - No Cleaning Fees!
14–21 Oct
€ 107 per night
Guest favourite
Flat in Chesapeake
4.95 out of 5 average rating, 41 reviewsBlissful Nook @ Washington
19–26 Aug
€ 120 per night
Guest favourite
Flat in Chesapeake
4.89 out of 5 average rating, 19 reviewsWarm Luxury unit Central Greenbrier
18–25 Jan
€ 163 per night
Guest favourite
Home in Norfolk
5.0 out of 5 average rating, 22 reviewsStylish Beach House, Hot Tub, Pet Friendly
17–24 Feb
€ 165 per night
Guest favourite
Bungalow in Chesapeake
4.93 out of 5 average rating, 72 reviewsPrivate and Cozy Bungalow Loaded with Amenities
13–20 May
€ 130 per night
Guest favourite
Guest suite in Chesapeake
4.91 out of 5 average rating, 46 reviewsGuest Suite with Private entrance & bathroom
11–18 Aug
€ 128 per night
Quick stats about holiday rentals in Chesapeake
Total rentals
1.1K 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
31K 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
- Rentals with a patio Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a cinema Chesapeake
- Rentals with a firepit Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Private suite rentals Chesapeake
- Apartment rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Waterfront rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Flat rentals Chesapeake
- House rentals Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with a fireplace Chesapeake
- Monthly Rentals Chesapeake
- Rentals with a hot tub Chesapeake
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