A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Western Massachusetts cottages

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

1. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is SAR 919
SAR 2,154 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake
A wooden deck with a table, benches, and outdoor furniture.

2. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is SAR 1,355
SAR 2,083 total
includes taxes & fees
8 Nov - 9 Nov
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

3. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is SAR 469
SAR 1,198 total
includes taxes & fees
26 Oct - 27 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A house with a deck, surrounded by trees and a grassy slope.

4. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is SAR 548
SAR 1,511 total
includes taxes & fees
11 Nov - 12 Nov
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A house by a lake with a dock and a boat.

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

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 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 698
SAR 1,091 total
includes taxes & fees
26 Oct - 27 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
An outdoor patio with a fire pit, a grill, and outdoor furniture.

6. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is SAR 743
SAR 1,412 total
includes taxes & fees
25 Oct - 26 Oct
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
A red building with a white door and windows, a concrete driveway, and a grassy area with a lake in the background.

7. 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, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is SAR 731
SAR 1,481 total
includes taxes & fees
28 Oct - 29 Oct
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A two-story house with a well-maintained lawn and mature trees.

8. 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 750
SAR 1,690 total
includes taxes & fees
22 Oct - 23 Oct
Sharon Retreat w/ Private Yard
A wicker hanging chair with a cushioned seat on a wooden deck overlooking a forested area.

9. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
The price is SAR 1,182
SAR 2,207 total
includes taxes & fees
27 Oct - 28 Oct
Waterfront Lake Cottage - Lake Access -Kayaks
A two-story house with a balcony, a chimney, and a window with a view.

10. 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 3,117
SAR 6,963 total
includes taxes & fees
18 Nov - 19 Nov
Berkshires farm, 30+ guests, 50 acres
A covered outdoor seating area with two chairs and a table, overlooking a snowy forest.

11. Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin
A cabin with a wooden deck, a covered porch, and a gravel driveway.

12. 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 840
SAR 2,079 total
includes taxes & fees
22 Oct - 23 Oct
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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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Top Western Massachusetts Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This is hands down my favorite hotel, and I have stayed here before and will keep coming back again and again! Everything about this place makes it feel special. The rooms are always spotless, incredibly spacious, and equipped with everything you need to feel right at home. Having a coffee maker, a full-size refrigerator, an oven, and a stove makes such a difference, especially for longer stays. The excellent jacuzzi is another big plus and makes it easy to relax and unwind. The property also has so many great amenities, and the surrounding nature is absolutely beautiful. There are plenty of amazing places to explore nearby, making it a perfect destination for a relaxing getaway while still having lots of things to do. What I love most is that the rooms feel more like a fully equipped apartment than a typical hotel room. It’s the kind of place where you can truly settle in, feel comfortable, and wish you could stay longer. I absolutely love this hotel, and it will always be one of my favorite places to stay. I will definitely be back again and again!"
Diana 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between SAR 1,091 and SAR 6,963 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 110 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.