Best Cottages in Western Massachusetts in 2026

A panorama of western Massachusetts from the top of Mount Greylock

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Our top choices for Western Massachusetts cottages

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

Stafford

Liz Y.

includes taxes & fees

1 Jun - 2 Jun

Brookside cottage near the mountains and outdoor recreation

Readsboro

Seva L.

includes taxes & fees

7 Jun - 8 Jun

Hiking Trails On-site: Cozy Falls Brook Cabin

Brattleboro

sarah

includes taxes & fees

15 Jun - 16 Jun

Trainmaster's Inn - Caboose

Palmer

Edward L.

includes taxes & fees

31 May - 1 Jun

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Rindge

Rebecca

includes taxes & fees

1 Jun - 2 Jun

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Stottville

includes taxes & fees

31 May - 1 Jun

Berkshires farm, 30+ guests, 50 acres

New Lebanon

includes taxes & fees

31 May - 1 Jun

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

includes taxes & fees

4 Jun - 5 Jun

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Top Western Massachusetts Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"The room was clean and comfortable, the staff was friendly and helpful..only negative is that the furniture in the room is in serious need of replacement… veneers on end tables lifting, upholstered kitchen chairs all had rips…"

Berkshires Untold

6/10 Okay

"The converted motel has several appealing features — it was clean, the Le Labo products smelled wonderful, and the lobby bar is beautifully designed. Unfortunately, the level of service fell well below expectations. Two days before our arrival, I received a survey asking whether we’d like any additional amenities, which initially gave me a very positive impression of the hotel’s attention to detail. However, upon check-in, not only was the requested amenity missing, but the room was also inadequately stocked: there was only one roll of toilet paper, a nearly empty tissue box with just three tissues remaining, and only two towels for three guests. I requested additional towels, but they were never delivered. The following morning, I asked again and was met with a dismissive, somewhat snarky response that they would arrive later. By 4 p.m., we still had not received them, and when I followed up, I was told my name was “on a list,” though no one could say when the towels would actually be available. Throughout the stay, the staff came across as indifferent rather than genuinely helpful, and service was often delivered with attitude rather than hospitality. While the hotel’s location is excellent and the property itself has charm, I left feeling unconvinced that the hotel currently has the staffing or linens needed to provide a truly top-tier guest experience."

Hotel UMass

8/10 Good

"Smack middle of campus. Ideal for touring UMass Amherst. You know where you are...the throw pillows and throw blanket on the beds were emblazoned with UMASS. Parking is not quite straight forward if you use GPS, but still easy to get to. Breakfast was a simple spread. Unfortunately, unable to adjust temperature of the room. There is no air conditioning in the room. I was told the building is central air?!"

Holiday Inn Express Springfield Downtown by IHG

8/10 Good

"Staff was nice and the room was clean. My only issue was being stuck in the elevator and not knowing how long it would take. The fire department had to get us out, it would have been nice to know we were waiting on the fire department. Even though it was only 20 to 30 minutes, it felt like forever."

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews	52
Accommodation	105 Cottages
Lowest Price	£177
Highest Price	£1,540

Frequently asked questions

How much do cottages in Western Massachusetts cost?

Cottages in Western Massachusetts range between £177 and £1,540 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 105 cottages to choose from. Enter your dates and destination and organise 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!

How can I find cheap cottages in Western Massachusetts?

Expedia can help you easily locate cheap cottages in Western Massachusetts. To lock in your perfect stay in a few clicks, simply use our handy filter tool to tailor your search results by budget, amenities and star rating.

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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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Western Massachusetts cottages

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

Brookside cottage near the mountains and outdoor recreation