Holiday houses 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
Apartment in Chesapeake
4.97 out of 5 average rating, 74 reviews1 King Master BR. ⚡️Fast Wifi. 🔐 Easy Self Check In
Guest favourite
Apartment in Chesapeake
5.0 out of 5 average rating, 32 reviewsEntire Apartment - No Cleaning Fees!
Guest favourite
Townhouse in Chesapeake
4.97 out of 5 average rating, 33 reviewsCenter of Greenbrier
Guest favourite
Home in Chesapeake
4.88 out of 5 average rating, 25 reviewsChesapeake. 3 Bedroom 1-1/2 Bath Small family home
Guest favourite
Bungalow in Chesapeake
4.93 out of 5 average rating, 75 reviewsPrivate and Cozy Bungalow Loaded with Amenities
Guest favourite
Condo in Chesapeake
5.0 out of 5 average rating, 5 reviews2BR Condo in Chesapeake - Western Branch
Guest favourite
Home in Norfolk
5.0 out of 5 average rating, 25 reviewsStylish Beach House, Hot Tub, Pet Friendly
Guest favourite
Home in Chesapeake
4.92 out of 5 average rating, 38 reviewsHidden Gem in Chesapeake, Virginia
Quick stats about accommodation 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 Accommodation & holiday rentals
- Virginia Beach Holiday rentals
- Richmond Accommodation & holiday rentals
- Norfolk Holiday rentals
- Williamsburg Accommodation & holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Accommodation & holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Accommodation & holiday rentals
- New York Accommodation & holiday rentals
- Jersey City Holiday rentals
- Rentals with a hot tub Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a home theatre Chesapeake
- Private suite rentals Chesapeake
- Condo rentals Chesapeake
- Rentals with pools Chesapeake
- Apartment rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Fitness-friendly rentals Chesapeake
- House rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with a fire pit Chesapeake
- Smoking-friendly rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with outdoor seating Chesapeake
- Monthly Rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with breakfast Chesapeake
- Waterfront rentals Chesapeake
- Townhouse rentals Chesapeake
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