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Vacation rentals in Ashfield

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Top-rated vacation rentals in Ashfield

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Rental unit in Shelburne Falls

4.95 out of 5 average rating, 195 reviews

Soaring 2-level loft w/ views in heart of downtown

Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

Guest suite in Greenfield

4.94 out of 5 average rating, 178 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Rental unit in Shelburne Falls

4.96 out of 5 average rating, 322 reviews

Annies’ Place by The Bridge of Flowers ~

As a guest at Annie’s Place, enjoy access to a tastefully, renovated 3 room apartment, including a fully equipped kitchen, living room, sofa with 2 recliners, a spacious bedroom, walk-in closet, full bath, TV & Internet. There is a seasonal front porch and mudroom for convenience. Meticulously maintained and located in the downtown village area. Simply park and walk to specialty shops, restaurants & the Bridge of Flowers. Shelburne Falls, designated as one of the 15 “Great Places in America.”

Guesthouse in Northampton

5 out of 5 average rating, 320 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Rental unit in Conway

4.95 out of 5 average rating, 139 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, then known as "Goat Meadow Farm". We hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Rental unit in Goshen

4.93 out of 5 average rating, 391 reviews

Experience Three Sisters Sanctuary

Stunning, artist-designed home surrounded by nature and centrally located to nearby cultural hubs and fine dining in Northampton and the Berkshires. Private apartment designed in the Arts and Crafts tradition accommodates 4 people with two bedrooms. Stay includes full access to 8-acres of enchanting healing sculpture gardens with fire pits for nighttime use. From recent review “There is really no way to know how peaceful, wonderous, and one of a kind this space is. Absolutely magical grounds.”

Cabin in Cummington

4.98 out of 5 average rating, 196 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Loft in Shelburne Falls

4.94 out of 5 average rating, 289 reviews

The Railroad House

The Railroad House is a cute attached converted barn in the village center with parking, private entrance, 2 floors, fridge, microwave, coffee maker, toaster, WiFI, but no television. It is located within just a minute's walk from the famous Bridge of Flowers. Other local attractions include several dining choices from a drugstore soda shop on up to 5-star dining, as well as the country's 2nd oldest bowling alley. On weekends you can often find live music. Train goes by twice/day on average.

Rental unit in Shelburne Falls

4.97 out of 5 average rating, 523 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Guest suite in Charlemont

4.9 out of 5 average rating, 198 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Rental unit in Plainfield

4.97 out of 5 average rating, 259 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Rental unit in Greenfield

4.96 out of 5 average rating, 360 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Small, cozy private Apt is located in West Greenfield in a quiet, save neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes

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Popular amenities for Ashfield vacation rentals

Free parking on premises

Air conditioning

Stay near Ashfield's top sights

Elmer's Store40 locals recommend

Ashfield Lakehouse37 locals recommend

DAR State Forest33 locals recommend

Three Sisters Sanctuary18 locals recommend

Countrypie Pizza Co.17 locals recommend

Double Edge Theatre16 locals recommend

Other great vacation rentals in Ashfield

Home in Ashfield

4.89 out of 5 average rating, 46 reviews

Luxury log style home with views to Mt. Monadnock!

Cabin in Guilford

4.96 out of 5 average rating, 511 reviews

Serenity Now - Couples Retreat or Writer's Dream

Guesthouse in Putney

4.97 out of 5 average rating, 270 reviews

Cozy cottage loft and retreat

Rental unit in Conway

5 out of 5 average rating, 12 reviews

Spacious, Sunny* Woodland Retreat

Rental unit in Northampton

4.92 out of 5 average rating, 592 reviews

Sunny Peaceful Home

Home in Ashfield

5 out of 5 average rating, 38 reviews

An 18th century farmhouse

Tiny home in Orange

4.92 out of 5 average rating, 346 reviews

The Writer's Retreat: A Sweetwater Stay

Home in Ashfield

4.97 out of 5 average rating, 73 reviews

Magical, Rural Getaway in the Berkshires

Quick stats about vacation rentals in Ashfield

Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

Do house rentals in Ashfield have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Ashfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ashfield have free parking?
Absolutely! We offer over 10 house rentals with free parking in Ashfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Ashfield?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Ashfield?
Yes! Work meets play with ease at over 10 vacation rentals in Ashfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Ashfield?
Four-legged friends are welcome in Ashfield. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Ashfield?
Experience the best of Ashfield with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Ashfield have wifi?
Absolutely! We offer over 10 house rentals with wifi in Ashfield. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Ashfield?
Ashfield has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore