Search Western Massachusetts Cottage Rentals from CA $205

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Check prices for these dates

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Jul 25 - Jul 27
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Browse Select Western Massachusetts Cottages

Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"2nd time here so I give it excellent review."
The price is CA $205
CA $385 total
includes taxes & fees
Jul 31 - Aug 1
Perfect Vacation Get Away - Historical New Marlborough
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Property grounds

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (39)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Interior

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (4)
"A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (192)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (110)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (3)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!
Massachusetts Vacation Rental w/ Deck
House (3 Bedrooms) | Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Private Island - Largest Fresh Water Reservoir in Mass....
Interior

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass....
Westfield Vacation Rental w/ Porch, Pets Welcome!
Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Beachwood Cottage
Interior

Beachwood Cottage

10.0 out of 10, Exceptional, (4)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Quiet rustic cottage with shared lake access
Fridge, microwave, oven, stovetop

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (108)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Historic Huntington Home - Walk to Westfield River
House (3 Bedrooms) | Private kitchen

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Grandparent’s Cottage 250 steps to the lake
Sun loungers, beach towels

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
Charlemont Retreat on Chickley River w/ EV Charger
Interior

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Cozy Springfield Vacation Rental Near Downtown
Terrace/patio

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is CA $274
CA $564 total
includes taxes & fees
Jul 15 - Jul 16
The Blue Elm - A Historic Berkshire Cottage
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Interior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (11)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Cavalier Cottage B&B
Exterior

Cavalier Cottage B&B

3.0 star property
9.0 out of 10, Wonderful, (2)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
Cavalier Cottage B&B
Cozy Becket Cottage Escape w/ Lake Access!
Cottage (2 Bedrooms) | Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
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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Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between CA $205 and CA $274 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 117 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!