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, 361 reviewsThe Nook
29 Nov – 6 Dec
£99 per night
Guest favourite
Guest suite in Carrollton
4.98 out of 5 average rating, 162 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
12–19 Mar
£94 per night
Guest favourite
Guest house in Hampton
4.99 out of 5 average rating, 288 reviewsSun Sea and Sand
17–24 Oct
£134 per night
Guest favourite
Home in Norfolk
4.92 out of 5 average rating, 156 reviews@Whit’s End? Come in and Relax
12–19 Oct
£91 per night
Guest favourite
Home in Virginia Beach
4.9 out of 5 average rating, 209 reviewsQuilted Quarters by the Bay with Private Entrance
23–30 Jan
£83 per night
Guest favourite
Guest suite in Chesapeake
4.99 out of 5 average rating, 136 reviewsBeautiful Two Bedroom King Bed Guest House
16–23 Jul
£293 per night
Guest favourite
Townhouse in Chesapeake
4.92 out of 5 average rating, 109 reviewsTasha's Townhouse *King, Queen, Twin*
4–11 Aug
£206 per night
Guest favourite
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
17–24 Dec
£107 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
- New York Holiday rentals
- Jersey City Holiday rentals
- Rentals with an EV charger Chesapeake
- Waterfront rentals Chesapeake
- Family-friendly rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a firepit Chesapeake
- Monthly Rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with lake access Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with pools Chesapeake
- Apartment rentals Chesapeake
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- Rentals with beach access Chesapeake
- Rentals with a fireplace Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a cinema Chesapeake
- Rentals with a patio Chesapeake
- House rentals Chesapeake
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