A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Western Massachusetts cottages

Terrace/patio

1. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.8 out of 10, Exceptional, (46 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
The price is AED 477
AED 1,213 total
includes taxes & fees
11 Sep - 12 Sep
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
House (3 Bedrooms) | Interior

2. 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
24 Aug - 25 Aug
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

3. 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)
"Cozy cabin with a big yard right on a beautiful lake."
United States
Adam a.
The price is AED 628
AED 1,411 total
includes taxes & fees
31 Aug - 1 Sep
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

4. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 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 764
AED 1,140 total
includes taxes & fees
6 Sep - 7 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Terrace/patio

5. 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, (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 AED 716
AED 1,455 total
includes taxes & fees
13 Sep - 14 Sep
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior

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 AED 4,441
AED 8,112 total
includes taxes & fees
8 Sep - 9 Sep
Berkshires farm, 30+ guests, 50 acres
House (4 Bedrooms) | Interior

7. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is AED 948
AED 2,797 total
includes taxes & fees
21 Aug - 22 Aug
Mtn-view Retreat in Huson Valley: Great for Groups
House (4 Bedrooms) | Interior

8. 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
20 Aug - 21 Aug
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

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Maintenance problems in room. Property made up for it."
Steve 1-night trip
Posted 7 hours ago
The Red Lion Inn

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between AED 1,140 and AED 8,112 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 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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