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Featured Cottages in Western Massachusetts

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is NZ$714
includes taxes & fees
5 Oct - 6 Oct
The Blue Elm - A Historic Berkshire Cottage

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (201)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
The Clearing - Quiet - Close To Nature

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (115)
"What a lovely property! And Rich was just terrific!"
Charming historic cottage on scenic road to Mt. Greylock

Light-filled cottage

10.0 out of 10, Exceptional, (1)
"Beautiful, well-designed home deserves a 10 out of 10 for aesthetics. Very glad Jing (the host) and her family are sharing this jewel of a home with the rest of us. Jing was a quick, kind and cordial communicator. The house location was quiet and tranquil. Nearby lake was within walking distance and delightful."
Light-filled cottage

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"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!

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

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

Cozy Springfield Vacation Rental Near Downtown

3.0 star property
Cozy Springfield Vacation Rental Near Downtown

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

9.4 out of 10, Exceptional, (15)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

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

Entire cottage in Berkshire Villiage

3.0 star property
9.6 out of 10, Exceptional, (7)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Quaint Massachusetts Home w/ Yard & Grill!

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

10.0 out of 10, Exceptional, (7)
"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

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

3.0 star property
10.0 out of 10, Exceptional, (1)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Beachwood Cottage

9.6 out of 10, Exceptional, (5)
"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

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

Private Lake Cottage on 3 acres w/350 sq. ft. deck

10.0 out of 10, Exceptional, (1)
"We spent a lovely, relaxing weekend in this well kept and well situated property. Hoping to come back again."
Private Lake Cottage on 3 acres w/350 sq. ft. deck
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

Find out more about Western Massachusetts

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
343
Accommodation
115 Cottages
Lowest Price
NZ$714
Highest Price
NZ$714

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between NZ$714 and NZ$714 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 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.

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