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Compare 110 Vacation Homes in Ashfield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 536
AED 821 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The house was originally built in 1864 and completely updated in 2009

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The Jelly Mill-A River Retreat
Green River Cottage. Walk up ramp to enter patio area, lockbox on inside door.

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
The Jelly Mill-A River Retreat
Amherst, Perfect Location, UMass, Smith, MHC!
The Valley is known for our picturesque red tobacco barns and expansive cornfields.

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

Charlemont Retreat on Chickley River w/ EV Charger

9.4 out of 10, Exceptional, (20)
"We loved the property! Our family, which included 2 very young grandchildren all felt comfortable in this historic home with 2 modern bathrooms. I loved the open kitchen and family rooms, and the original wide plank floors. Plus, we were happy to find toys to entertain the 3 year old. The owners were very gracious and responsive. Visitors should just be aware that the owners' unit shares a common wall with the house. Dog barking and sounds of their kitchen preparation were evident through the...
Charlemont Retreat on Chickley River w/ EV Charger
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Marina

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Plainfield House in a 10,000 acre state forest and private pond
Front lawn for sledding

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (84)
"Very nice place, clean, great communication. "
Plainfield House in a 10,000 acre state forest and private pond
Charming 4Bds+1crib house with patio Amherst Center
Pool

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location near restaurants and stores. House is "
The price is AED 760
AED 1,538 total
includes taxes & fees
29 Dec - 30 Dec
Charming 4Bds+1crib house with patio Amherst Center
Cozy apartment located in quiet Williamsburg
Exterior

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is AED 551
AED 940 total
includes taxes & fees
27 Dec - 28 Dec
Cozy apartment located in quiet Williamsburg
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
View of house as seen from road near the brook

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Hadley Amherst Location.Explore the Valley Colleges!
Bike ride on the Norwottuck Rail Trail( entrance to trail 2-minutes from the house) to the CT River- Bring your bikes and enjoy!

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (129)
"The house was amazing, clean and comfortable. The area was great and very close to restaurants and shopping. I just can’t say enough good things about our experience. If I could give it more than five stars I would. "
Hadley Amherst Location.Explore the Valley Colleges!
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Best night's sleep on king size sleigh bed

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (96)
"Easy check in, very clean and well stocked with everything needed. I was visiting my daughter at UMass who had to have knee surgery. There was lots of space for her to get around. It was also close to the University which was important for us as well."
The price is AED 533
AED 763 total
includes taxes & fees
30 Dec - 31 Dec
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Welcome to our Whitingham Wonderland. Enjoy gas fireplace, smart tv, cozy throws

Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!

10.0 out of 10, Exceptional, (26)
"The house was perfect for a group of five of us. The kitchen and grill were great for our culinary needs. Thanks for letting us stay!"
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Welcome! Plenty of space to yourselves to relax and soak in great outdoors!

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (76)
"Very cute and quiet location! Cabin has everything ine would need! Plenty of parking, and there are trails throughout the property. Its in the perfect spot, only 18 minutes from town. "
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
A full kitchen with almost everything you need to cook your favorite dishes.

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (20)
"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Aerial view

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

9.8 out of 10, Exceptional, (8)
" The home has everything that you could possibly need. The host was great in checking in to make sure our stay was going well and if we needed anything. The beds were comfortable, the living room spacious and a great place to hang out. The house was spotless. The outdoor area is beautiful and a fantastic place to enjoy the beautiful setting. Best VRBO that I have stayed at, we are hoping to make a return trip. Would highly recommend!"
The price is AED 823
AED 1,979 total
includes taxes & fees
7 Jan - 8 January 2025
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Pittsfield Vacation Rental | 3BR | 2.5BA | 2,000 Sq Ft | 2 Steps Required

Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!

9.0 out of 10, Wonderful, (2)
"This was an amazing rental everything was amazing, I can't wait to book this property again"
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Lovely Contemporary Vermont Home
Snowbound & Cozy...

Lovely Contemporary Vermont Home

10.0 out of 10, Exceptional, (5)
"Enjoyed our stay."
Lovely Contemporary Vermont Home
Peaceful Family Home w/ Fire Pit & Large Yard
Williamstown Vacation Rental | 3BR | 3BA | 2 Stories | 2,400 Sq Ft

Peaceful Family Home w/ Fire Pit & Large Yard

10.0 out of 10, Exceptional, (15)
"This is a gorgeous, welcoming, and very comfortable home. If we could give it more than five stars we would! And it's a great home base for exploring the beautiful Berkshires. "
Peaceful Family Home w/ Fire Pit & Large Yard
1770 House - An end of a dirt road hideaway where you can relax and unwind.
Exterior

1770 House - An end of a dirt road hideaway where you can relax and unwind.

10.0 out of 10, Exceptional, (1)
"Views are outstanding. Kitchen is incredibly well stocked. Beds are comfortable. Swimming pool is a super good time. Lots of space in this house to enjoy with family and friends. Very convenient to center of Greenfield. Looking forward to staying there again."
1770 House - An end of a dirt road hideaway where you can relax and unwind.
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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Other property types in Ashfield

Sunny Chalet Nestled in the Woods of Ashfield
Dining

Sunny Chalet Nestled in the Woods of Ashfield

9.6 out of 10, Exceptional, (14)
"We were all very rested and relaxed. We enjoyed the beautiful spaces to sit and enjoy each other’s company. The chalet, flowers and setting made a terrific base to come and go from as we celebrated a family wedding."
Sunny Chalet Nestled in the Woods of Ashfield
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 536
AED 821 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.