A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Western Massachusetts cottages

A wooden deck with a table, benches, and outdoor furniture.

1. 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 CA $506
CA $784 total
includes taxes & fees
Nov 8 - Nov 9
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.

2. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
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 CA $175
CA $453 total
includes taxes & fees
Nov 10 - Nov 11
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
A house with a deck, surrounded by trees and a grassy slope.

3. 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 CA $204
CA $564 total
includes taxes & fees
Nov 4 - Nov 5
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A wooden deck with two chairs and a table, overlooking a lake with trees in the background.

4. 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 CA $273
CA $549 total
includes taxes & fees
Oct 28 - Oct 29
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.

5. 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 CA $280
CA $634 total
includes taxes & fees
Oct 28 - Oct 29
Sharon Retreat w/ Private Yard
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 CA $1,215
CA $2,659 total
includes taxes & fees
Nov 18 - Nov 19
Berkshires farm, 30+ guests, 50 acres
Two Adirondack chairs facing a river with a grassy area and trees in the background.

7. Waterfront Lake Cottage - Lake Access -Kayaks

Waterfront Lake Cottage - Lake Access -Kayaks
Avon
The price is CA $441
CA $817 total
includes taxes & fees
Nov 2 - Nov 3
Waterfront Lake Cottage - Lake Access -Kayaks
A cabin with a wooden deck, a covered porch, and a gravel driveway.

8. 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 CA $356
CA $823 total
includes taxes & fees
Oct 28 - Oct 29
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
"Great"
Anna 1-night trip
Posted 2 hours ago
Vacation Village in the Berkshires

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
112
Accommodation
116 Cottages
Lowest Price
CA $453
Highest Price
CA $2,659

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between CA $453 and CA $2,659 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 116 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.
What is there to do in Western Massachusetts near my cottage?
The most important travel accessory for your Western Massachusetts trip is a well-organized itinerary! Titanic Museum, Springfield Armory and Springfield City Library are some of the well-known sights if you're heading to Springfield. West Springfield is also packed with wonderful attractions, such as Big E. Need more travel inspo? Find time for Eastern States Exposition and Olympia Ice Center too.

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