A lake with a rocky shoreline and a forested island.

Search Western Massachusetts Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Western Massachusetts cottages

A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is AU$454
includes taxes & fees
20 Sept - 21 Sept
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A house with a deck, surrounded by trees and a grassy slope.

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
The price is AU$564
includes taxes & fees
5 Oct - 6 Oct
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A house by a lake with a dock and a boat.

3. 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 AU$409
includes taxes & fees
21 Sept - 22 Sept
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A red cabin with a stone patio, a grill, and a view of a lake.

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)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is AU$539
includes taxes & fees
17 Sept - 18 Sept
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
An outdoor patio with a fire pit, a grill, and outdoor furniture.

5. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is AU$560
includes taxes & fees
13 Oct - 14 Oct
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
A two-story house with a balcony, a chimney, and a window with a view.

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 AU$2,697
includes taxes & fees
5 Oct - 6 Oct
Berkshires farm, 30+ guests, 50 acres
A cabin with a wooden deck, a covered porch, and a gravel driveway.

7. 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 AU$776
includes taxes & fees
21 Sept - 22 Sept
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A wooden deck leading to a house with a view of a road and greenery.

8. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
The price is AU$1,094
includes taxes & fees
21 Sept - 22 Sept
Spacious Vermont Farmhouse 3 Mi to Mount Snow
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Western Massachusetts Hotel Reviews

Hotel UMass

Hotel UMass

10/10 Excellent
"Great rooms!"
Matthew 1-night trip
Posted 9 hours ago
Hotel UMass

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
88
Accommodation
113 Cottages
Lowest Price
AU$409
Highest Price
AU$2,697

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Prepare to pay between AU$409 and AU$2,697 per night for cottages in Western Massachusetts. Whatever your budget, an epic stay is only a few clicks away on Expedia. This price was 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?
You can select from 113 cottages in Western Massachusetts. Whether you're travelling with the kids, as a twosome or with a group of pals, Expedia makes it a cinch to find your ideal place.
What is there to do in Western Massachusetts near my cottage?
The best accessory to pack for your Western Massachusetts adventure is a well-designed itinerary! Naismith Memorial Basketball Hall of Fame, Titanic Museum and Springfield Science Museum are some of the top sights if you're on your way to Springfield. Amherst is also home to impressive attractions, such as Emily Dickinson Museum. In the mood to explore more? Check out Amherst Farm Winery and Mead Art Museum too.

Explore a world of travel with Expedia