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/peaceful-spacious-lodge-with-golf-sunset-views/HA-3213250039" class="class="static-page-link"">Peaceful, Spacious Lodge with Golf &amp; Sunset Views</a> <a href="/property/angel-mist-retreat-garage-apartment/HA-3213147277" class="class="static-page-link"">Angel Mist Retreat Garage Apartment</a> <a href="/property/the-cozy-home-new-comfortable-centrally-located/HA-3214849838" class="class="static-page-link"">The Cozy Home- New, Comfortable, Centrally located</a> <a href="/property/cozy-home-in-pittsfield/BC-14987628" class="class="static-page-link"">Cozy Home in Pittsfield</a> <a href="/property/golfer-s-getaway-luxury-studio-next-to-1st-tee/HA-3213265210" class="class="static-page-link"">Golfer&#39;s Getaway - Luxury Studio Next to 1st Tee</a> <a href="/property/pine-tree-trail-lodge/EP-121376376" class="class="static-page-link"">Pine Tree Trail Lodge</a> <a href="/property/riverside-loft-cozy-1br-w-sebasticook-river-views-trail-access-wi-fi/HA-3214936059" class="class="static-page-link"">Riverside Loft – Cozy 1BR w/Sebasticook River Views &amp; Trail Access + Wi-Fi</a> <a href="/property/hubs-hideaway-a-warm-inviting-3-bedroom-2-bath-home-recently-renovated/HA-3214879728" class="class="static-page-link"">Hubs Hideaway - a warm inviting 3 bedroom, 2 bath home. Recently renovated!</a> <a href="/property/superb-2-bedroom-home-with-ac-in-detroit/HA-3215023504" class="class="static-page-link"">Superb 2-bedroom Home with AC in Detroit</a> <a href="/property/riverbend-loft-modern-stay-near-atv-snowmobile-trails/HA-3214936058" class="class="static-page-link"">RiverBend Loft | Modern Stay Near ATV &amp; Snowmobile Trails</a>

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

The average cost for a cottage rental in Pittsfield is $167 per night. Inclusiveholidays 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: Cozy cabin with 200’ of waterfront on Whites Pond Palmyra Cottage with Deck on Whites Pond! Palmyra Cottage w/Deck on Whites Pond! Peaceful, Spacious Lodge with Golf & Sunset Views Cozy Home in Pittsfield Pine Tree Trail Lodge Angel Mist Retreat Garage Apartment <a href="/all/usa/maine/pittsfield" class="class="static-page-link"">See all pet-friendly vacation rentals in Pittsfield on Inclusiveholidays</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 Inclusiveholidays shows that there are Over 3 private swimming pools or cottages with indoor pools in the Pittsfield area along with other great amenities.

Pittsfield Cottage Rentals By Owner

Cozy cabin with 200’ of waterfront on Whites Pond

From US $128

9.6 (41 Reviews)

Cottage

Cozy cabin with 200’ of waterfront on Whites Pond

Air Conditioner
Parking
Pet Friendly

Pittsfield Cottage Rentals & Holiday Homes

Find the best cottages in Pittsfield - We found 3 exact matches

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