A lake with a rocky shoreline and a forested island.

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Our top choices for Western Massachusetts cottages

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 €495
includes taxes & fees
18 Nov - 19 Nov
The Cottage on Mill Brook is walking distance to Berkshire East and the River.

2. 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
Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3. 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, (50 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is €271
includes taxes & fees
10 Nov - 11 Nov
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

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)
"Excellent property, really enjoyed this beautiful home."
United States
Susan G.
The price is €326
includes taxes & fees
5 Nov - 6 Nov
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

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 €419
includes taxes & fees
13 Nov - 14 Nov
Sharon Retreat w/ Private Yard

6. 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.
Waterfront Lake Cottage - Lake Access -Kayaks

7. 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 €1,760
includes taxes & fees
19 Nov - 20 Nov
Berkshires farm, 30+ guests, 50 acres

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 €524
includes taxes & fees
18 Nov - 19 Nov
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

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
114
Accommodation
116 Cottages
Lowest Price
€271
Highest Price
€1,760

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between €271 and €1,760 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 organise 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-organised itinerary! Titanic Museum, Springfield Armoury 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 Centre too.

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