Holiday Rentals Western Massachusetts from £76: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Western Massachusetts holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Pittsfield

marilyn

includes taxes & fees

9 Nov - 10 Nov

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Williamstown

Pofen

includes taxes & fees

1 Nov - 2 Nov

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

3. Lovely 2nd Floor Apartment

Greenfield

Jane P.

includes taxes & fees

1 Nov - 2 Nov

A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

4. Serene 1-bedroom suite on 75 acre horse property

Belchertown

Wayne B.

includes taxes & fees

18 Oct - 19 Oct

A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

5. Modern Studio Ideal for Traveling Professionals

Holyoke

Kebreab H.

includes taxes & fees

13 Oct - 14 Oct

A cozy room with two beds, large windows, and a view of a snowy landscape.

6. The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.

Paula

includes taxes & fees

13 Oct - 14 Oct

A blue house with a porch, a wooden bench, and a door.

7. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Greenfield

Andrew R.

includes taxes & fees

25 Oct - 26 Oct

8. Modern Studio Ideal for Traveling Professionals

Holyoke

includes taxes & fees

13 Oct - 14 Oct

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Top Western Massachusetts Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"This is my go-to accommodation to visit Williams College in Williamstown."

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

Quality Inn Great Barrington

8/10 Good

"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"

Find out more about Western Massachusetts

Everything you need to know about Western Massachusetts holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Western Massachusetts holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Western Massachusetts holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Western Massachusetts holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Western Massachusetts. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Western Massachusetts holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Western Massachusetts holiday rentals we have selected for you start as low as £76 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Western Massachusetts rentals

At Expedia, we put the best Western Massachusetts holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Western Massachusetts rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Western Massachusetts holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Western Massachusetts. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Western Massachusetts holiday rentals

1. Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

3. Lovely 2nd Floor Apartment

4. Serene 1-bedroom suite on 75 acre horse property

5. Modern Studio Ideal for Traveling Professionals

6. The Creation Station is a cozy place so make yourself at home.

7. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

8. Modern Studio Ideal for Traveling Professionals

9. Newly Built Barn Loft in Pioneer Valley

10. Work, Play & Stay! Apt Near Holyoke Medical Center

11. 2 Twin beds on 1st floor with En-suite bathroom.

12. Downtown | Waterfront | Walk to Shops

13. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

14. Charming, updated 3 bedroom farmhouse farm stay.

15. Button's Modern Luxury Walkup Downtown Northampton

16. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

17. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

18. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

19. New Studio In Town, By the Water

20. Private bed with En-suite bathroom Marigold Room

Find holiday rentals that suit your style

Top Western Massachusetts Hotel Reviews

Vacation Village in the Berkshires

Find out more about Western Massachusetts

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