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Check prices for these dates

Next weekend
9 Jan - 11 Jan
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16 Jan - 18 Jan
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30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Western Massachusetts cottages

Living area
Beautiful 2-bedroom cottage on Robert Frost Trail

Cottage in Amherst

Beautiful 2-bedroom cottage on Robert Frost Trail
2.0 star property
The price is NZ$497
includes taxes & fees
11 Jan - 12 Jan 2026
Beautiful 2-bedroom cottage on Robert Frost Trail
Private kitchen
Trainmaster's Inn - Caboose

Cottage in Palmer

Trainmaster's Inn - Caboose
9.4 out of 10, Exceptional, (10)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is NZ$582
includes taxes & fees
1 Jan - 2 Jan 2026
Trainmaster's Inn - Caboose
Property grounds
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Cottage in Stafford

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
9.6 out of 10, Exceptional, (30)
"Great host- fun property!"
United States
Mary F.
The price is NZ$440
includes taxes & fees
5 Jan - 6 Jan 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
House (3 Bedrooms) | Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
Wilmington Retreat Near Trails, Skiing & Festivals
Exterior
Pet-Friendly Hudson Escape w/ Hot Tub

Cottage in Stottville

Pet-Friendly Hudson Escape w/ Hot Tub
2.0 star property
The price is NZ$605
includes taxes & fees
20 Jan - 21 Jan 2026
Pet-Friendly Hudson Escape w/ Hot Tub
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Cottage in Rindge

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (22)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is NZ$629
includes taxes & fees
5 Jan - 6 Jan 2026
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Terrace/patio
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is NZ$627
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Exterior
Berkshires farm, 30+ guests, 50 acres

Cottage in New Lebanon

Berkshires farm, 30+ guests, 50 acres
2.0 star property
The price is NZ$3,032
includes taxes & fees
12 Jan - 13 Jan 2026
Berkshires farm, 30+ guests, 50 acres
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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
Stephanie 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
63
Accommodation
110 Cottages
Lowest Price
NZ$440
Highest Price
NZ$3,032

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between NZ$440 and NZ$3,032 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 110 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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