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, 147 reviewsCentrally Located Sleek Studio Apartment
6–13 Jan
£86 per night
Guest favourite
Home in Norfolk
4.92 out of 5 average rating, 154 reviews@Whit’s End? Come in and Relax
9–16 Apr
£100 per night
Guest favourite
Guest house in Yorktown
4.97 out of 5 average rating, 203 reviewsCharming Yorktown Battlefield Cottage
12–19 Aug
£102 per night
Guest favourite
Flat in Williamsburg
4.84 out of 5 average rating, 360 reviewsThe Nook
8–15 Nov
£95 per night
Guest favourite
Guest house in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
17–24 Mar
£158 per night
Guest favourite
Guest suite in Virginia Beach
4.99 out of 5 average rating, 309 reviewsJust Steps Away to the Beach
21–28 Jul
£151 per night
Guest favourite
Guest suite in Virginia Beach
4.85 out of 5 average rating, 171 reviewsSmall & Cozy Guest Suite w/ Private Bath & Jet-Tub
17–24 May
£84 per night
Guest favourite
Guest suite in Virginia Beach
4.89 out of 5 average rating, 550 reviewsQuiet Neighborhood 7 Miles From the Beaches
2–9 Nov
£87 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
- Monthly Rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a patio Chesapeake
- Apartment rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Waterfront rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a firepit Chesapeake
- Private suite rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- House rentals Chesapeake
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- Family-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with a fireplace Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with a cinema Chesapeake
- Rentals with outdoor seating Chesapeake
- Smoking-friendly rentals Chesapeake
- Flat rentals Chesapeake
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