A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Western Massachusetts cottages

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 AED 551
AED 1,272 total
includes taxes & fees
5 Jul - 6 Jul
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, (41 reviews)
"Very nice area."
United States
maureen p.
The price is AED 551
AED 1,305 total
includes taxes & fees
7 Jul - 8 Jul
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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 AED 823
AED 2,035 total
includes taxes & fees
5 Jul - 6 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
The price is AED 698
AED 1,493 total
includes taxes & fees
22 Jul - 23 Jul
Perfect for a peaceful get away in clean fresh Vermont air!
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 AED 1,327
AED 1,858 total
includes taxes & fees
5 Jul - 6 Jul
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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 AED 4,143
AED 8,082 total
includes taxes & fees
7 Jul - 8 Jul
Berkshires farm, 30+ guests, 50 acres
House (4 Bedrooms) | Interior

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is AED 1,396
AED 2,400 total
includes taxes & fees
5 Jul - 6 Jul
3 Mi to Mount Snow: Spacious West Dover Home
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

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

10/10 Excellent
"Very nice place and nice staff"
Tangy 2-night trip
Posted 4 hours ago
Holiday Inn Express Springfield Downtown by IHG

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between AED 1,272 and AED 8,082 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 124 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.

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