Search Cottages in Western Massachusetts

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Cabins
Cabins
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Aparthotels
Aparthotels

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Western Massachusetts cottages

A house by a lake with a dock and a boat.

1. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (14 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
United States
clifford t.
The price is SAR 658
SAR 986 total
includes taxes & fees
16 Nov - 17 Nov
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A cabin with a wooden deck, a covered porch, and a gravel driveway.

2. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is SAR 953
SAR 2,205 total
includes taxes & fees
16 Nov - 17 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A wooden deck with two chairs and a table, overlooking a lake with trees in the background.

3. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (26 reviews)
"Excellent property, really enjoyed this beautiful home."
United States
Susan G.
The price is SAR 732
SAR 1,405 total
includes taxes & fees
16 Nov - 17 Nov
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

4. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
The price is SAR 810
SAR 1,747 total
includes taxes & fees
16 Nov - 17 Nov
Sharon Retreat w/ Private Yard
Two Adirondack chairs facing a river with a grassy area and trees in the background.

5. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
10.0 out of 10, Exceptional, (1 review)
"The cottage is very cozy, private, and in a beatiful setting. We really appreciated the upgrades that made our stay comfortable. The fenced-in yard was great for our dog. Take a note of a stone floor on the lower level. We had to cover it to be not too cold for the dog to lie on (in late October). The location is right on the water for kayaking and close to some well maintained trails for biking and hiking."
United States
Victoria F.
The price is SAR 1,182
SAR 2,197 total
includes taxes & fees
8 Dec - 9 Dec
Waterfront Lake Cottage - Lake Access -Kayaks
A two-story house with a balcony, a chimney, and a window with a view.

6. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is SAR 3,340
SAR 6,827 total
includes taxes & fees
16 Nov - 17 Nov
Berkshires farm, 30+ guests, 50 acres
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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Learn more about Western Massachusetts

Rolling hills and charming towns define this picturesque region, where art lovers flock to MASS MoCA in North Adams. Outdoor enthusiasts can hike Mount Greylock, while history buffs explore Norman Rockwell's studio in Stockbridge.

See all hotels in Western Massachusetts
A panoramic view of a valley with autumn foliage, a town in the distance, and rolling hills.

Top reviews in Western Massachusetts

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
Egremont

10/10 Excellent

So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
United States
Emily
Reviewed July 7, 2025
Prospect Berkshires

Frequently Asked Questions

How much do cottages in Western Massachusetts cost?

Cottages in Western Massachusetts range between SAR 657 and SAR 3,340 per night. These stays offer a chance to reconnect with nature — at a price you can afford. 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?

Western Massachusetts has cottages to choose from. Enter your dates and destination and organize your ideal getaway today.

Why book your cottage in Western Massachusetts with Expedia?

Reserving a cottage in Western Massachusetts is as easy as entering your travel dates and picking your ideal place for a getaway in nature. From luxurious retreats to low-cost stays and cottages that come with perks like a hot tub, Expedia has something for all styles. As for irresistible deals? We've got you covered!

How can I find cheap cottages in Western Massachusetts?

Expedia can help you easily locate cheap cottages in Western Massachusetts. To lock in your perfect stay in a few clicks, simply use our handy filter tool to tailor your search results by budget, amenities and star rating.