We found 597 vacation rentals — enter your dates for availability
Discover a selection of 500 vacation rentals in Chesterwood, Stockbridge that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $90 per night, and houses and cabins are popular options for a stay in Chesterwood. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Chesterwood
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How many vacation rentals are available around Chesterwood, Stockbridge?
Our 2021 property listings offer a large selection of 597 vacation rentals around Chesterwood. From 432 house rentals to 61 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.
Can I rent Houses near Chesterwood?
Yes, of course. Vrbo has 432 Houses near Chesterwood. Our other popular types of vacation rentals near Chesterwood include:
- Cabins: 61 rentals available
- Condos/Apartments: 79 rentals available
- Cottages: 61 rentals available
But you can also enjoy a great stay in one of our other vacation rentals including Country houses and more.
Can I find a vacation rental with pool near Chesterwood?
Yes, you can select your preferred vacation rental with pool among our 149 vacation rentals with pool available near Chesterwood. Please use our search bar to access the selection of vacation rentals available.
Can I book a vacation rental directly online or instantly near Chesterwood?
Yes, Vrbo offers a selection of 597 vacation rentals to book directly online and 218 with instant booking available near Chesterwood. Don't wait, have a look at our vacation rentals via our search bar and be ready for your next trip near Chesterwood!