What are the top rated Cottage Rentals in Pittsfield?

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: <a href="/property/berkshire-lake-beauty-modern-amenities-on-the-lake/HA-3211439982" class="class="static-page-link"">Berkshire Lake Beauty-Modern Amenities On The Lake</a> <a href="/property/tranquil-lake-house-getaway-on-onota-lake/HA-3211335967" class="class="static-page-link"">Tranquil Lake House Getaway on Onota Lake</a> <a href="/property/casa-do-lago-waterfront-home-with-private-dock-on-pontoosuc-lake/HA-321723295" class="class="static-page-link"">Casa Do Lago-Waterfront Home With Private Dock On Pontoosuc Lake</a> <a href="/property/lakeside-home-with-pool-completely-renovated/HA-3212154688" class="class="static-page-link"">Lakeside Home With Pool-Completely Renovated</a> <a href="/property/escape-to-your-cozy-retreat-near-pontoosuc-lake-and-jiminy-peak/HA-3213218564" class="class="static-page-link"">Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak</a> <a href="/property/ray-of-sunshine-berkshire-home-on-pontoosuc-lake/HA-3213847344" class="class="static-page-link"">Ray of Sunshine Berkshire Home on Pontoosuc Lake</a> <a href="/property/charming-lakeview-cottage-in-heart-of-the-berkshires/HA-3214434066" class="class="static-page-link"">Charming Lakeview Cottage in Heart of the Berkshires</a> <a href="/property/spacious-luxury-berkshire-s-estate-on-21-acres/HA-3214335236" class="class="static-page-link"">Spacious Luxury Berkshire&#39;s Estate on 21 acres</a> <a href="/property/berkshires-lake-view-hot-tub-large-open-great-room-lrg-kitchen/HA-3213182216" class="class="static-page-link"">Berkshires Lake View, Hot Tub, Large Open Great Room, Lrg Kitchen</a> <a href="/property/charming-1-bedroom-4-star-resort-w-heated-pool-gym-wi-fi-lot-s-more/HA-3214111196" class="class="static-page-link"">Charming 1 Bedroom - 4 Star Resort w/heated pool, gym, wi-fi, lot&#39;s more!</a>

How much does it cost to rent a cottage in Pittsfield?

The average cost for a cottage rental in Pittsfield is $391 per night. Cruiseandresorts 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.

Are there any cottages in Pittsfield that allow pets?

Yes, here are the top cottage rentals in Pittsfield that allow you to bring your pet: A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything Elegant Pittsfield Home Near Downtown and Skiing! Berkshire Mountain Lodge Lake Front Home in Heart of the Berkshires Near Jiminy Peak <a href="/all/usa/massachusetts/pittsfield" class="class="static-page-link"">See all pet-friendly vacation rentals in Pittsfield on Cruiseandresorts</a>

Do you have any rental cottages in Pittsfield that are suitable for families?

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.

Are there quality cottages in Pittsfield that have indoor swimming pools?

As of 2026, the data from Cruiseandresorts shows that there are Over 105 private swimming pools or cottages with indoor pools in the Pittsfield area along with other great amenities.

Pittsfield Cottage Rentals By Owner

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

From US $342

10.0 (129 Reviews)

Cabin

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Air Conditioner
Parking
TV

Pittsfield Cottage Rentals & Holiday Homes

Find the best cottages in Pittsfield - We found 105 exact matches

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