Western Massachusetts, MA Vacation Homes from AED 759

A lake with a rocky shoreline and a forested island.

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Our top choices for Western Massachusetts vacation homes

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

1. Lovely 2nd Floor Apartment

Greenfield

Jane P.

AED 919 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Easthampton Ma.

Paula

AED 1,030 total

includes taxes & fees

3 Nov - 4 Nov

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

3. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

AED 759 total

includes taxes & fees

9 Nov - 10 Nov

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

4. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

AED 1,596 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

Sherwood Forest

Sharon K.

AED 1,382 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

6. Cozy Home in Holyoke with 3 bedrooms

Holyoke

Grant J.

AED 1,321 total

includes taxes & fees

21 Oct - 22 Oct

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

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

Sherwood Forest

Frank M.

AED 1,445 total

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a bed, curtains, a bedside table, and a lamp.

8. Townhouse with Pool Table - Renovated w/ King Bed

Chicopee

Nicholas B.

AED 1,589 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Sherwood Forest

William C B.

AED 1,128 total

includes taxes & fees

3 Nov - 4 Nov

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

10. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

AED 1,320 total

includes taxes & fees

22 Oct - 23 Oct

A hallway with wooden flooring, white walls, and a bed in the background.

11. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

AED 1,531 total

includes taxes & fees

21 Oct - 22 Oct

A dining area with a round table, four chairs, and a kitchen in the background.

12. Cozy 2-Bedroom Springfield Home 1.5 Baths

Six Corners

AED 913 total

includes taxes & fees

21 Oct - 22 Oct

A modern living room with a sofa, a coffee table, and a red patterned rug.

13. Cozy & Spacious Entire Home in Springfield

Forest Park

Brian

AED 1,265 total

includes taxes & fees

25 Oct - 26 Oct

A living room with two brown leather sofas, a glass coffee table, a white rug, a ceiling fan, and a door with curtains.

14. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Boston Road

Beth P.

AED 1,433 total

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

15. Home in Great Barrington

Great Barrington

Janet G.

AED 1,239 total

includes taxes & fees

3 Nov - 4 Nov

A kitchen with white cabinets, a wooden dining table, and pendant lights.

16. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

AED 1,764 total

includes taxes & fees

30 Oct - 31 Oct

A living room with two sofas, a coffee table, and a potted plant.

17. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Boston Road

Angelina O.

AED 1,433 total

includes taxes & fees

21 Oct - 22 Oct

A staircase with a wooden handrail and a white wall with a light switch.

18. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

AED 1,036 total

includes taxes & fees

26 Oct - 27 Oct

A dining area with a long wooden table set for six, surrounded by chairs. There are hanging pendant lights above the table.

19. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Amherst

Emily Robustelli K.

AED 5,970 total

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

20. Amherst -NEW - Campus Convenience & Social Privacy

Amherst

Kimberly D.

AED 2,773 total

includes taxes & fees

5 Nov - 6 Nov

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Top Western Massachusetts Hotel Reviews

Berkshires Untold

10/10 Excellent

"Great service"

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Hotel Downstream in North Adams was a great location for our overnight get-away to bike the Ashuwillticook Rail Trail. The hotel is right down-town, so we were able to walk to Public for dinner and to Bright Ideas Brewery afterwards, and to Dino's for breakfast in the morning. The room was very large and clean. We had a nice view of downtown and the mountains. Staff was very friendly -- we had a very quick check-in and check-out. Parking is right there and free. All very convenient. The hotel only serves continental breakfast, so we chose to go out, but it's nice that they provide water, coffee, tea and fruit all day long."

Vacation Village in the Berkshires

8/10 Good

"I liked the location and the room itself very much. I thought the price was good too. Only real complaint is the pool is very busy and smallish for the amount of families the place can hold. Also, the pool isnt connected from what i could tell so you have to drive or take a walk to and from your roomafrom i"

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Economy Car Rentals in Williamsburg

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Western Massachusetts vacation homes

1. Lovely 2nd Floor Apartment

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

3. Private bed with En-suite bathroom Marigold Room

4. Charming, updated 3 bedroom farmhouse farm stay.

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

6. Cozy Home in Holyoke with 3 bedrooms

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

8. Townhouse with Pool Table - Renovated w/ King Bed

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

10. Big farmhouse in the foothills of the Berkshires

11. Cozy private 2 bed apartment in Shelburne Falls

12. Cozy 2-Bedroom Springfield Home 1.5 Baths

13. Cozy & Spacious Entire Home in Springfield

14. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

15. Home in Great Barrington

16. A roomy remodeled retreat close to MassMoCA

17. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

18. Leaf-Peeper Paradise in the Berkshires

19. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

20. Amherst -NEW - Campus Convenience & Social Privacy

Find vacation rentals that suit your style

Top Western Massachusetts Hotel Reviews

Berkshires Untold

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Williams Inn

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

Vacation Village in the Berkshires

D. Hotel Suites & Spa

Hotel On North

Explore a world of travel with Expedia

Search Vacation Homes in Western Massachusetts

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Western Massachusetts vacation homes

1. Lovely 2nd Floor Apartment

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

3. Private bed with En-suite bathroom Marigold Room

4. Charming, updated 3 bedroom farmhouse farm stay.

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

6. Cozy Home in Holyoke with 3 bedrooms

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

8. Townhouse with Pool Table - Renovated w/ King Bed

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

10. Big farmhouse in the foothills of the Berkshires

11. Cozy private 2 bed apartment in Shelburne Falls

12. Cozy 2-Bedroom Springfield Home 1.5 Baths

13. Cozy & Spacious Entire Home in Springfield

14. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

15. Home in Great Barrington

16. A roomy remodeled retreat close to MassMoCA

17. Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

18. Leaf-Peeper Paradise in the Berkshires

19. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

20. Amherst -NEW - Campus Convenience & Social Privacy

Find vacation rentals that suit your style

Top Western Massachusetts Hotel Reviews

Berkshires Untold

Explore a world of travel with Expedia