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Featured Cottages in Ashfield

Massachusetts Vacation Rental w/ Deck
Interior

Massachusetts Vacation Rental w/ Deck

3.0 star property
Massachusetts Vacation Rental w/ Deck
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Fireplace

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
2 bedrooms, iron/ironing board, bed sheets

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Charlemont Retreat on Chickley River w/ EV Charger
Terrace/patio

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Jacksonville Cabin w/ Wraparound Deck & Views
Interior

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Historic Huntington Home - Walk to Westfield River
Private kitchen

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
'john's Farmhouse in Mount Snow' on 120 Acres!
5 bedrooms, laptop workspace, free cribs/infant beds, bed sheets

'john's Farmhouse in Mount Snow' on 120 Acres!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
TV, fireplace

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Peaceful Family Home w/ Fire Pit & Large Yard
Private kitchen

Peaceful Family Home w/ Fire Pit & Large Yard

3.0 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
Private kitchen

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

3.0 star property
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!
Hadley Vacation Rental 24 Mi to Springfield!
Private kitchen

Hadley Vacation Rental 24 Mi to Springfield!

3.0 star property
Hadley Vacation Rental 24 Mi to Springfield!
Cozy Southern Vermont Home w/ On-site Trails
Exterior

Cozy Southern Vermont Home w/ On-site Trails

3.0 star property
Cozy Southern Vermont Home w/ On-site Trails
Picturesque Cottage With Sunroom on Ashmere Lake!
Interior

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Interior

Lakefront Westhampton Cabin w/ Beach + Kayaks!

3.0 star property
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Quaint Massachusetts Home w/ Yard & Grill!
Microwave, oven, stovetop, dishwasher

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Quaint Massachusetts Home w/ Yard & Grill!
Massachusetts Vacation Rental w/ Deck & Grill
4 bedrooms, laptop workspace, bed sheets

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill
Home 15 Mi to Berkshire East & Mount Snow!
Interior

Home 15 Mi to Berkshire East & Mount Snow!

3.0 star property
Home 15 Mi to Berkshire East & Mount Snow!
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Interior

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

3.0 star property
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Outdoor dining

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

3.0 star property
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
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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Frequently asked questions

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Expedia can help you track down cheap cottages in Ashfield. To find a terrific stay in a matter of clicks, try out the filter tool to tailor your search results by star rating, amenities and budget.
What is there to do in Ashfield near my cottage?
No matter your interests, Ashfield has a whole lot to keep you on the move. Double Edge Theatre, Ashfield Lake and Land of Providence are on most visitors’ sightseeing plans. Don’t forget to check out Chapel Brook, Bullitt Reservation and Ashfield Plain Cemetery either. With Expedia’s Ashfield hotel deals, you can discover more neat attractions like these with the money you save.