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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Western Massachusetts cottages

Interior

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!
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, (37 reviews)
"Great location, beautiful view completely relaxing "
United States
Carlos T.
The price is HK$1,159
HK$2,717 total
includes taxes & fees
18 May - 19 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 HK$1,286
HK$2,067 total
includes taxes & fees
18 May - 19 May
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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 HK$1,175
HK$2,685 total
includes taxes & fees
18 May - 19 May
Trainmaster's Inn - Caboose
Terrace/patio

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is HK$1,723
HK$3,192 total
includes taxes & fees
31 May - 1 Jun
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
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 HK$1,374
HK$2,885 total
includes taxes & fees
20 May - 21 May
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 HK$1,057
HK$1,859 total
includes taxes & fees
20 May - 21 May
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 HK$9,601
HK$18,121 total
includes taxes & fees
21 May - 22 May
Berkshires farm, 30+ guests, 50 acres
Interior

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
The price is HK$1,198
HK$3,212 total
includes taxes & fees
15 Jun - 16 Jun
Hiking Trails On-site: Cozy Falls Brook Cabin
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 HK$1,198
HK$4,084 total
includes taxes & fees
18 May - 19 May
Outdoor Adventure Hub! Family Home in West Dover
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 HK$1,535
HK$4,335 total
includes taxes & fees
18 May - 19 May
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Interior

Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
3.0 star property
Windsor
The price is HK$1,919
HK$4,547 total
includes taxes & fees
18 May - 19 May
Spacious Yard w/ Gazebo: Charming Windsor Retreat
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The staff is wonderful!"
Leslie 1-night trip
Posted 6 hours ago
The Red Lion Inn

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
74
Accommodation
115 Cottages
Lowest Price
HK$1,859
Highest Price
HK$18,121

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between HK$1,859 and HK$18,121 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 115 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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