Pittsfield Cottage Rentals & Golf course

Find the best cottages in Pittsfield - We found 61 exact matches

About Pittsfield Cottage Rentals on StayAndPlay

Looking for exceptional golf cottages near Pittsfield for your next getaway? StayAndPlay offers more than 61 unique golf retreats and luxury villas, perfect for your family or group trip. Discover accommodations set in scenic golf destinations, featuring amenities like private pools, championship course access, and spacious living areas. These rentals provide an exceptional experience, catering to families, friends, couples, or golf enthusiasts.

Planning a golf retreat or a getaway for your group? StayAndPlay provides a variety of accommodations, including top-rated golf cottages, private villas, and spacious vacation rentals, connecting you directly with property owners to secure the best rates.

Explore 61 premium golf stays and exclusive golf-friendly accommodations in Pittsfield with StayAndPlay. Find unique Airbnb-style and VRBO-style golf rentals perfect for your weekend escape, golf vacation, or corporate retreat, all within your budget.

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Frequently Asked Questions About Pittsfield Rental Cottages

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 Cottage Rentals in Pittsfield:

The average cost for a cottage rental in Pittsfield is $663 per night. StayAndPlay.com has a wide list of great cottages near Pittsfield that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Pittsfield that allow you to bring your pet:

See all pet-friendly vacation rentals in Pittsfield on StayAndPlay

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Pittsfield to find one that works for you.
As of 2025, the data from StayAndPlay shows that there are Over 61 private swimming pools or cottages with indoor pools in the Pittsfield area along with other great amenities.
About 61 cottages in Pittsfield boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Pittsfield on StayAndPlay
Yes, there are luxury cottages in Pittsfield. Find more luxury, lakefront, winter, & last-minute cottage rentals near Pittsfield.