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Holiday rentals in Ashfield

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Top-rated holiday rentals in Ashfield

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Guest favourite
The well-equipped kitchen features wooden cabinetry, stainless-steel appliances, and a dining area with a round wooden table and four chairs. Natural light enters through a large window, illuminating the polished wooden floors and enhancing the open layout connecting to the living area.
Flat in Shelburne Falls

Sunny, shiny downtown flat w/mountain+river views

Walk to everything from this sunny, spacious, tastefully furnished apartment in the 1893 Vice Building, newly renovated in 2023, in the heart of downtown, steps from Bridge of Flowers. Giant windows in all directions with views of town, mountains & river. Queen bedroom & comfy pull-out queen bed in living room. Large, well-equipped eat-in kitchen w/ brand-new stainless-steel appliances & dishwasher. Washer/dryer. Luxurious bathtub & rain shower. Lots of closet space. Fast Internet. 65" Roku TV.

4.89 out of 5 average rating, 228 reviews
Top guest favourite
Guest house in Cummington

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

4.99 out of 5 average rating, 222 reviews
Top guest favourite
The bright studio features a cozy sleeping area with a spacious bed, a comfortable yellow armchair, and two plush couches. A coffee table sits in the center, with large windows allowing natural light and views of greenery. A television is mounted on the wall.
Flat in Shelburne Falls

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!

4.97 out of 5 average rating, 659 reviews
Top guest favourite
A functional kitchen is presented, featuring stainless steel appliances, including a refrigerator and oven. Light-colored cabinets offer storage space, while a countertop spaces is visible. The room is accented by soft blue walls, providing a calm backdrop to the cooking area.
Guest house in Shelburne Falls

Shelburne Guest House -The Ranch

The nice thing about my home in Shelburne is the location & the peace & quiet. 10 minute drive to Greenfield Rotary I-91, easy drive to Amherst, Smith, UMass, NMH, Deerfield Academy & Stoneleigh Burnham School. Berkshire East nearby for outdoor sports. 5 minute drive to the Village of Shelburne Falls, hiking trails, bike paths, High Ledges, & the Bridge of Flowers. Updated 1964 Sears Roebuck catalog home. Bright & sunny! Large farmhouse kitchen, 3 cozy bedrooms. Large yard! Porch!

5.0 out of 5 average rating, 318 reviews
Top guest favourite
The living room features a high, vaulted ceiling with large, triangular windows allowing ample natural light. A brick fireplace serves as a focal point, surrounded by a wooden mantel and decorative plants. A dining table sits nearby, and hardwood flooring is complemented by colorful area rugs.
Farm stay in Ashfield

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

5.0 out of 5 average rating, 155 reviews
Top guest favourite
A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.
Home in Ashfield

An 18th century farmhouse

Built in 1785 this antique Cape was carefully restored to its original design about 20 years ago. The house is set on a quiet road in the middle of fields, woods, gardens, and hiking trails. it is secluded with easy access to the natural world. The rooms are book-lined and filled with family objects. It is close to Berkshire East for skiing and snowboarding in the winter and whitewater rafting and swimming in the summer. Mass MoCA and the Clark Museum are within an easy drive.

4.97 out of 5 average rating, 110 reviews
Top guest favourite
A bright living area is highlighted by a slanted ceiling and a pellet stove, offering warmth and comfort. Two black chairs are positioned on a patterned rug, while a sectional sofa provides spacious seating. Natural light filters through a skylight and window adorned with light curtains.
Flat in Plainfield

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!

4.97 out of 5 average rating, 312 reviews
Top guest favourite
A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.
Flat in Conway

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, having 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.

4.96 out of 5 average rating, 228 reviews
Top guest favourite
A row of trees with vibrant autumn leaves stands against a clear blue sky. The sunlight filters through the branches, creating a warm glow, while long shadows stretch across a field blanketed in fallen leaves.
Farm stay in Ashfield

Blue House Farm and Gardens

Your lovely peaceful Studio shares a wall with our 1794 farmhouse but has its own entrance, porch and privacy. Enjoy the tranquility of our land but still be only 2.4 miles from the center of Ashfield, 30 minutes from Northampton and Old Deerfield, less than 20 minutes to Berkshire East Mountain Resort, 30 minutes to Notchview for cross country skiing and snowshoeing, and 45 minutes to Mass. MOCA.

4.98 out of 5 average rating, 105 reviews
Top guest favourite
A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.
Cabin in Plainfield

Peaceful Cabin in the Woods

Escape the noise and come relax in the middle of the beautiful Berkshire Hills. This classic log cabin has been recently renovated so that you can unwind and connect to the picturesque landscape that envelopes this property. You can drive 30 minutes west to North Adams and visit Mass Moca or 30 minutes east to Northampton, Amherst & Hadley. (Please note, 1/2 of the bedrooms is an open loft).

4.92 out of 5 average rating, 258 reviews
Top guest favourite
An open living area is highlighted by large windows that allow natural light to fill the space, which features a dark sofa and a wooden coffee table. A small plant sits on the floor, adding a touch of greenery to the room.
Cottage in Ashfield

hope house

Sunny and open writing studio with over 150 years of literary history. Built in 1870, this lovely little house was where George Curtis edited Harper's magazine, wrote essays on transcendentalism , and argued for women's suffrage ( A recent guest informs me that George Curtis helped Thoreau build his cabin on Walden Pond ) The house has since sheltered painters, librarians, and poets.

4.96 out of 5 average rating, 389 reviews
Guest favourite
A serene farmhouse sits amidst lush greenery, featuring a light green exterior and a charming porch. The surrounding landscape includes tall trees and dense foliage, creating a natural and tranquil setting. A chimney is visible, indicating a cozy interior.
Home in Ashfield

Magical, Rural Getaway in the Berkshires

Serene, idyllic, and extensively renovated farmhouse. Perfect for bird watchers, outdoor enthusiasts, and those seeking a tranquil retreat. Large kitchen (2 skylights) w new D/W & Fridge. Downstairs bath with w/d. DAR Forest (lake), Chapel Falls (waterfall). as well as Ashfield Lake. Fast/reliable fiber w/bakup battery. Pet (dog) fee: $150. Sorry, no cats.

4.95 out of 5 average rating, 106 reviews

Popular amenities for Ashfield holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Ashfield's top sights

Chapel Falls

22 locals recommend

Bear Swamp

4 locals recommend

Daughters of the American Revolution State Forest

3 locals recommend

Other great holiday rentals in Ashfield

Top guest favourite
A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.
Flat in Northampton

Light filled three bedroom apartment DT Florence!

4.97 out of 5 average rating, 499 reviews
Top guest favourite
The living area features a cozy sectional sofa and an armchair, arranged around a coffee table on a soft area rug. Light-colored walls are complemented by wooden accents, and artwork adorns the walls. Natural light is provided by large windows dressed with light drapes.
Home in Ashfield

J&J’s Retreat

5.0 out of 5 average rating, 35 reviews
Guest favourite
A serene view of a house set amongst lush greenery, reflected on calm water. The architecture includes a sloped roof and multiple windows, framed by trees that provide natural shade and a sense of seclusion.
Home in Ashfield

Pondside Retreat - Entire House

4.88 out of 5 average rating, 16 reviews
Top guest favourite
A dining area is illuminated by natural light from large windows. A table with a floral tablecloth is surrounded by metal chairs. Two comfortable armchairs are positioned nearby, and a desk with a computer is situated against the wall, creating a welcoming space for relaxation.
Flat in Conway

Spacious, Sunny* Woodland Retreat

4.99 out of 5 average rating, 92 reviews
Top guest favourite
A rustic log cabin-style retreat is surrounded by lush greenery and ferns. The exterior features a combination of wood siding and a red metal roof, with multiple levels and expansive windows allowing for natural light. The grounds offer a serene, natural environment.
Home in Ashfield

Luxury log style home with views to Mt. Monadnock!

4.92 out of 5 average rating, 62 reviews
Top guest favourite
Home in Shelburne Falls

Bridge of flowers cottage

4.98 out of 5 average rating, 92 reviews
Top guest favourite
The charming exterior of the 18th-century farmhouse features yellow clapboard siding and a classic red front door. Symmetrical windows line the facade, surrounded by a manicured lawn and the shade of nearby trees.
Farm stay in Whately

Beautiful 18th Century Farmhouse

5.0 out of 5 average rating, 41 reviews
Top guest favourite
A living area is depicted, featuring a gray sectional sofa paired with a complementary armchair. A wooden coffee table sits at the center, adorned with coasters. Background elements include an open kitchen area with modern appliances and a lightly lit shelf showcasing decorative items.
Flat in Shelburne Falls

Downtown Modern Apartment

5.0 out of 5 average rating, 88 reviews

Destinations to explore