Pittsfield Holiday Homes
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Featured Holiday Homes in Pittsfield

Pet Friendly Riverfront Home in Great Barrington

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Peace and quiet on the lake

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Riverbend Berkshire East Basecamp - 3 bedrooms available

Berkshire House Stay

Amore Estate - beautiful room with many places to explore and relax in.

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Holiday Accommodation Pittsfield
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Pittsfield are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Pittsfield itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Pittsfield holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Pittsfield, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Pittsfield with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Pittsfield Holiday Homes essential information
Accommodation | 421 Holiday Homes |
|---|---|
Lowest Price | NZ$154 |
Highest Price | NZ$1,899 |
Popular accommodation | Pet Friendly Riverfront Home in Great Barrington, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Peace and quiet on the lake, Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Riverbend Berkshire East Basecamp - 3 bedrooms available, Berkshire House Stay, Amore Estate - beautiful room with many places to explore and relax in., Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!, A Grand property in Historic Stockbridge |
Top trending hotels in Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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