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 kitchens. Prices start at $214 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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How many vacation rentals are available around Chesterwood, Stockbridge?

Our 2020 property listings offer a large selection of 630 vacation rentals around Chesterwood. From 369 house rentals to 74 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 369 Houses near Chesterwood. Our other popular types of vacation rentals near Chesterwood include:

  • Cabins: 74 rentals available
  • Condos/Apartments: 80 rentals available
  • Cottages: 74 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Estates and more.

Can I find a vacation rental with pool near Chesterwood?

Yes, you can select your preferred vacation rental with pool among our 161 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 630 vacation rentals to book directly online and 219 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! 

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