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1 Aug - 3 Aug
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Featured Cottages in Western Massachusetts

Perfect Vacation Get Away - Historical New Marlborough
Cozy cabin with a small porch and Adirondack chairs, surrounded by lush greenery.

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"Lovely place!"
The price is NZ$437
includes taxes & fees
31 July - 1 Aug
Perfect Vacation Get Away - Historical New Marlborough
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cozy cabin surrounded by lush greenery, featuring a rustic exterior and a spacious garage.

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
Situated in a grassy area, this cozy home features a red-framed door and windows with string lights.

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
Set amidst mature trees, this home offers a serene atmosphere.

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
Cozy home surrounded by lush vegetation.

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (111)
"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
East Otis Vacation Rental w/ Private Deck & BBQ!
Escape to a secluded cabin surrounded by mature trees, featuring a cozy porch and deck with seating area.

East Otis Vacation Rental w/ Private Deck & BBQ!

9.6 out of 10, Exceptional, (8)
"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"
East Otis Vacation Rental w/ Private Deck & BBQ!
Lake Views & Dock Access - Pittsfield Cottage!
Traditional homes line the quiet street, each with a central chimney and green shutters.

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
Outdoor dining

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Private Island - Largest Fresh Water Reservoir in Mass....
Relax by the fire pit in this serene outdoor seating area overlooking the water.

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!
Stylish single-story home with a gabled roof and a cozy front porch.

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Beachwood Cottage
Stroll through the serene garden, surrounded by lush trees and shrubs, and discover a tranquil atmosphere perfect for relaxation.

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
Set amidst a serene natural setting, this home features a stone chimney, large windows, and a two-car garage.

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (109)
"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
Stunning home surrounded by lush greenery, featuring a stone pathway and charming lantern-style lights.

Historic Huntington Home - Walk to Westfield River

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."
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
Situated in a wooded area, this charming home offers a front porch with outdoor seating and a chimney.

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
Enjoy outdoor dining or relaxation on the porch, surrounded by a serene lawn and mature trees.

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 NZ$676
includes taxes & fees
5 Aug - 6 Aug
The Blue Elm - A Historic Berkshire Cottage
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Surrounded by lush greenery, this two-story house offers a welcoming outdoor space with a deck and porch.

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!
Guests can enjoy the cabin's expansive deck with seating and large windows offering a view of the surrounding forest.

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
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
"."
Rachid 1-night trip
Posted 23 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 NZ$437 and NZ$676 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 122 cottages to choose from. Enter your dates and destination and organise your ideal getaway today.
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.