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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Western Massachusetts cottages

Interior

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is £404
includes taxes & fees
13 Apr - 14 Apr
12-acre Vacation Rental in the Berkshires!
Living area

Beautiful 2-bedroom cottage on Robert Frost Trail

Beautiful 2-bedroom cottage on Robert Frost Trail
Amherst
The price is £243
includes taxes & fees
13 Apr - 14 Apr
Beautiful 2-bedroom cottage on Robert Frost Trail
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is £259
includes taxes & fees
16 Apr - 17 Apr
Trainmaster's Inn - Caboose
Terrace/patio

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, (34 reviews)
"Great location, beautiful view completely relaxing "
United States
Carlos T.
The price is £214
includes taxes & fees
30 Apr - 1 May
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (12 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is £228
includes taxes & fees
19 Apr - 20 Apr
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Living area

Backyard Tiny House in the Woods

Backyard Tiny House in the Woods
Tolland
The price is £107
includes taxes & fees
28 Apr - 29 Apr
Backyard Tiny House in the Woods
Terrace/patio

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
Stottville
The price is £228
includes taxes & fees
16 Apr - 17 Apr
Pet-Friendly Hudson Escape w/ Hot Tub
House (4 Bedrooms) | Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is £387
includes taxes & fees
13 Apr - 14 Apr
Outdoor Adventure Hub! Family Home in West Dover
Terrace/patio

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (23 reviews)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is £265
includes taxes & fees
23 Apr - 24 Apr
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (1 review)
"This place is simply fantastic. If you are looking for quiet...and I mean ABSOLUTE quiet...this is your place! Nestled just five minutes south of Readsboro, VT, Brookside Cottage is the place to get disconnected and just breathe a bit. Our family needed this place...I needed to be here...with our kids growing up so fast, now at 14 and 11, my wife and I just wanted to have a few days to be together, play some games, watch some movies, and enjoy each other's company. I'm convinced we found the...
United States
Jason H.
The price is £218
includes taxes & fees
15 Apr - 16 Apr
Brookside cottage near the mountains and outdoor recreation
Exterior

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 £1,342
includes taxes & fees
4 May - 5 May
Berkshires farm, 30+ guests, 50 acres
House (3 Bedrooms) | Interior

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 £411
includes taxes & fees
13 Apr - 14 Apr
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
House (4 Bedrooms) | Interior

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
3.0 star property
Newfane
The price is £427
includes taxes & fees
13 Apr - 14 Apr
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Spacious, clean, and the pool was warm and perfect for family swimming "
Danielle 2-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
70
Accommodation
105 Cottages
Lowest Price
£107
Highest Price
£1,342

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between £107 and £1,342 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 105 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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