Western Massachusetts Vacation Rentals from ￥17,385: Search Short-Term Rentals

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Our top choices for Western Massachusetts vacation rentals

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

1. Berkshire Mountain Lodge

Pittsfield

Robert

￥17,385 total

includes taxes & fees

Oct 1 - Oct 2

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

2. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Holyoke

￥37,236 total

includes taxes & fees

Sep 12 - Sep 13

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

3. Vacation Village in the Berkshires

Williamstown

Alex

￥18,321 total

includes taxes & fees

Sep 15 - Sep 16

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

4. Lovely 2nd Floor Apartment

Greenfield

Christa B.

￥31,612 total

includes taxes & fees

Sep 8 - Sep 9

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

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

Easthampton Ma.

Paula

￥43,461 total

includes taxes & fees

Sep 14 - Sep 15

6. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Holyoke

Michelle

￥37,701 total

includes taxes & fees

Sep 12 - Sep 13

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

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

Dalton

Elizabeth G.

￥50,530 total

includes taxes & fees

Sep 10 - Sep 11

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

8. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Anonymous traveler

￥65,870 total

includes taxes & fees

Sep 8 - Sep 9

A modern kitchen with a central island, bar stools, and a bicycle.

9. Button's Modern Luxury Walkup Downtown Northampton

Northampton

AMY

￥77,685 total

includes taxes & fees

Sep 8 - Sep 9

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

Holyoke

Jeremy R.

￥50,793 total

includes taxes & fees

Sep 29 - Sep 30

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

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

Sherwood Forest

Sharon K.

￥58,612 total

includes taxes & fees

Sep 8 - Sep 9

A hot tub with a string of lights above it, set against a dark night sky.

12. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

￥60,601 total

includes taxes & fees

Sep 8 - Sep 9

A house with a porch, a garden with pink flowers, and a stone wall along the road.

13. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

￥55,002 total

includes taxes & fees

Sep 8 - Sep 9

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

14. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

￥46,778 total

includes taxes & fees

Sep 13 - Sep 14

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

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

Greenfield

Meredith B.

￥45,625 total

includes taxes & fees

Sep 21 - Sep 22

A living room with a sofa set, a coffee table, and two lamps.

16. Cozy First Floor Apartment. Located in a quiet neighborhood.

Chicopee

Morrris

￥47,687 total

includes taxes & fees

Sep 13 - Sep 14

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

17. Rose room Victorian home queen bed private bath

Shelburne Falls

￥30,108 total

includes taxes & fees

Sep 10 - Sep 11

18. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

￥33,336 total

includes taxes & fees

Sep 8 - Sep 9

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

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

Belchertown

"This was an amazing nightly rate for the region, and a lovely place to visit. I'm so glad we found it and was available! Brent and family take great care of the place, and it was so magical waking up and seeing horses just a few feet from the window. We had fun playing games under the gazebo while horses munched on hay. There's lots of good hiking in the area too. The suite had everything we needed like extra blankets, kitchen wares, games, and a great shower too. Highly recommended!"

Elizabeth

￥41,745 total

includes taxes & fees

Sep 16 - Sep 17

A living room with a flat-screen TV, a ceiling fan, a sofa, a coffee table, and a decorative vase.

20. Charming Chicopee Getaway

Chicopee

Tamara S.

￥38,433 total

includes taxes & fees

Sep 9 - Sep 10

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Top Western Massachusetts Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"It was a beautiful property. Would definitely go again"

The Yankee Inn

10/10 Excellent

"On an overpriced holiday weekend in the Berkshires, Yankee Inn was a great balance of price and amenities. The indoor pool was nicer than most, and the hot tub was great. Outdoor pool was a bit oddly placed between the parking lot and the main road, but nice as well. Both very clean. Room was spacious and clean, beds were comfortable, though I think they were doubles rather than queens. The included breakfast was on the very good end of standard - the fruit was fresh and delicious, there were both eggs and waffles, plus cereal, yogurt, bacon/sausage. Meh on the pastries, and the coffee was terribly watery. My true only gripe is that there was truly not a single place to hang wet bathing suits that didn't result in them dripping all over the floor. Had we been on the 2nd floor, we would have had an outside railing, but on the first floor there was none. With 4 people using the pool and hot tub, it was an annoyance. Overall, great place for a quick stay."

Find out more about Western Massachusetts

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Check prices for these dates

Our top choices for Western Massachusetts vacation rentals

1. Berkshire Mountain Lodge

2. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

3. Vacation Village in the Berkshires

4. Lovely 2nd Floor Apartment

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

6. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

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

8. Charming, updated 3 bedroom farmhouse farm stay.

9. Button's Modern Luxury Walkup Downtown Northampton

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

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

12. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

13. Big farmhouse in the foothills of the Berkshires

14. Real Estate: Therapy - Lake, Laundry, Love it

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

16. Cozy First Floor Apartment. Located in a quiet neighborhood.

17. Rose room Victorian home queen bed private bath

18. Private bed with En-suite bathroom Marigold Room

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

20. Charming Chicopee Getaway

Find vacation 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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