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 Newport News
4.97 out of 5 average rating, 148 reviewsCentrally Located Sleek Studio Apartment
18–25 Jan
€ 100 per night
Guest favourite
Guest house in Yorktown
4.97 out of 5 average rating, 203 reviewsCharming Yorktown Battlefield Cottage
5–12 Oct
€ 113 per night
Guest favourite
Townhouse in Chesapeake
4.88 out of 5 average rating, 110 reviews2BR-1.5 Bath Electric & Vibrant R&R Townhome
27 Aug – 3 Sep
€ 226 per night
Guest favourite
Home in Virginia Beach
4.9 out of 5 average rating, 208 reviewsQuilted Quarters by the Bay with Private Entrance
4–11 Dec
€ 96 per night
Guest favourite
Townhouse in Chesapeake
4.92 out of 5 average rating, 109 reviewsTasha's Townhouse *King, Queen, Twin*
3–10 Aug
€ 239 per night
Guest favourite
Barn in Virginia Beach
4.79 out of 5 average rating, 831 reviewsCozy craftsman barn near the bay!
28 Mar – 4 Apr
€ 109 per night
Guest favourite
Flat in Williamsburg
4.84 out of 5 average rating, 361 reviewsThe Nook
14–21 Nov
€ 111 per night
Guest favourite
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
4–11 Dec
€ 124 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 washing machine and dryer Chesapeake
- Rentals with lake access Chesapeake
- House rentals Chesapeake
- Rentals with a patio Chesapeake
- Rentals with a fireplace Chesapeake
- Pet-friendly rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a firepit Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Waterfront rentals Chesapeake
- Monthly Rentals Chesapeake
- Flat rentals Chesapeake
- Family-friendly rentals Chesapeake
- Apartment rentals Chesapeake
- Rentals with beach access Chesapeake
- Smoking-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with breakfast Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a cinema Chesapeake
- Rentals with pools Chesapeake
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