Pittsfield Summer Rentals, Cottages & Cabins

Book a Place to Stay in Pittsfield for Your Summer Getaway

About Pittsfield Summer Rental on Rent By Owner

With 310 summer rentals in or near Pittsfield, choosing a suitable rental home for your upcoming summer getaway on Rent By Owner is easy. Whether you are traveling with family, friends, or in a group to Pittsfield or areas nearby, RBO has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.

Looking for a relaxing place to stay in Pittsfield for a summer vacation you do not want to forget easily? Rent By Owner summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Pittsfield, RBO has got you covered for your next summer holiday.

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Frequently Asked Questions About Pittsfield Luxury Rentals

There are a lot of options in Pittsfield. If you plan on staying in the Pittsfield area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Pittsfield:

In 2025, RBO offers 310 summer rentals in or around Pittsfield. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Pittsfield is $993. Check the full list of summer accommodations in Pittsfield.
There are 310 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rent By Owner.

Yes, here are some popular summer holiday rentals in Pittsfield that have a private or indoor pool:

Check all holiday rentals with a pool in Pittsfield on Rent By Owner.