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

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 563
SAR 851 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (21)
"Our family had a wonderful stay. The house was very comfortable and the owner was very responsive. The sound of the river right outside was delightful! The bathrooms are very nicely updated - a nice perk when staying in an older home. "
Charlemont Retreat on Chickley River w/ EV Charger

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 SAR 544
SAR 776 total
includes taxes & fees
12 Jan - 13 Jan
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

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!

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

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location near restaurants and stores. House is "
The price is SAR 884
SAR 1,704 total
includes taxes & fees
7 Feb - 8 Feb
Charming 4Bds+1crib house with patio Amherst Center

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!

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

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

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

10.0 out of 10, Exceptional, (28)
"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!

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (86)
"Simply fantastic!"
Hearts Desire is a furnished whole house in a small, colorful garden center.

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (17)
"As advertised, easy check-in, good location"
Massachusetts Vacation Rental w/ Deck

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.4 out of 10, Exceptional, (6)
"Location is minutes away from town. Location was easy to find. House was very clean and had all that we needed. Perfect size for our group of 5 adults, each having our own bedroom. We found plenty to do in the area. Jane was very helpful giving us information of things to do, especially being a girl's weekend, she informed us of spas, shopping and great spots to see foliage, and nice restaurant nearby that had music. Would definitely stay here again."
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

10.0 out of 10, Exceptional, (18)
"What a great place to share the Thanksgiving holiday with love ones! The setting is beautiful and was very comfortable."
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

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..

10.0 out of 10, Exceptional, (21)
"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..

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (17)
"Nice place on a quiet street. Stay went perfect "
The price is SAR 447
SAR 767 total
includes taxes & fees
13 Jan - 14 Jan
Lovely 2nd Floor Apartment

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

9.4 out of 10, Exceptional, (3)
"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

10.0 out of 10, Exceptional, (6)
"We had a wonderful extended family holiday visit. The property is spacious, well-appointed, and a blast for kids— inside playing games and outside playing in the snow. The fireplace was great, especially after dark as temps fell. The communications and instructions were helpful and clear. We would visit again!"
Lovely Contemporary Vermont Home
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

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!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 563
SAR 851 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!

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.