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Featured Cottages in Western Massachusetts

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River

Spacious & Modern Ashley Falls Home on 1 Acre

3.0 star property
8.0 out of 10, Very good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Spacious & Modern Ashley Falls Home on 1 Acre

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

3.0 star property
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Berkshires Cabin 2 Mi to Appalachian Trail!

3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

3.0 star property
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

Springfield Vacation Rental: 1 Mi to Downtown

3.0 star property
Springfield Vacation Rental: 1 Mi to Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Western Massachusetts

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is S$237
includes taxes & fees
27 Jan - 28 Jan
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (923)
"Staff was exceptionally helpful and friendly."
The price is S$279
includes taxes & fees
26 Jan - 27 Jan
Jiminy Peak Mountain Resort

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is S$351
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Rates for cottages in Western Massachusetts range between and per night. No matter your budget, you’re sure to find the perfect place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Western Massachusetts?
Take a look at our 60 cottages in Western Massachusetts and lock in your favourite. Whether you’re taking off on a holiday with the fam or a break with pals, your ideal stay is just a few clicks away with Expedia.
Why book your cottage in Western Massachusetts with Expedia?
Booking a cottage in Western Massachusetts is as easy as working out your travel dates and choosing an ideal place for a getaway in nature. From luxurious retreats to budget-friendly properties and cottages that include perks like free WiFi, Expedia has something for all styles and tastes. As for unbeatable deals? We’ve have them as well!
How can I find cheap cottages in Western Massachusetts?
With Expedia’s convenient filter tool, locating cheap cottages in Western Massachusetts is a breeze. To view properties that’ll make your bank balance smile, refine your search by amenities, star rating and budget.
What is there to do in Western Massachusetts near my cottage?
Whatever you’re interested in, there are many things to see and do in Western Massachusetts. If you’re bound for Springfield, be sure to look around Naismith Memorial Basketball Hall of Fame, Titanic Museum and Springfield Science Museum. Taking off to Amherst? Emily Dickinson Museum, Amherst Farm Winery and Mead Art Museum are among the best sights here.