Vacation rentals in Pioneer Valley

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Top-rated vacation rentals in Pioneer Valley

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A functional kitchen is showcased with custom wood cabinetry and a dark countertop. An electric stove and an overhead vent are visible, alongside open shelving displaying bowls and kitchen items. Natural light enters through a large window above the sink, illuminating the vibrant yellow walls.

Apartment in Leeds

4.98 out of 5 average rating, 153 reviews

Private Studio for a Sweet Getaway!

A cozy, comfortable, studio flat with ready access to local music venues and restaurants. Downtown Northampton is 15 mins by car or a 1/2 hr bike ride. We abut the bike path and there's a Valley Bike Share kiosk nearby. Ideal overnight spot for visiting Smith and other area colleges or for attending workshops at Snow farm. Easy day trips the Berkshires. Plenty of area hiking! Perfect personal retreat spot! I accept dogs on a case by case basis, small dogs preferred and I cannot accept cats.

Guest favorite

A bathroom space featuring light-colored wall tiles and a wooden floor. A white toilet is positioned against a wall. A small wooden bench adds functionality. A framed artwork is mounted on the wall, providing a decorative element. Natural light fills the area from an unseen source.

Guest suite in Northampton

4.87 out of 5 average rating, 553 reviews

Separate apt, 1 mile from downtown, 1 guest only

This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Top guest favorite

An open door reveals the entryway of a rustic cabin. A patterned rug leads into a softly lit interior, where a cozy bed is visible in the background, framed by natural wood accents and windows that invite the outside in.

Cabin in Cummington

4.98 out of 5 average rating, 219 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.

Top guest favorite

A spacious deck is surrounded by rustic wooden siding, featuring a circular table covered with a blue and white checkered tablecloth. Two Adirondack chairs, a grill for outdoor cooking, and potted plants offer a welcoming space beneath the shade of a large tree.

Guest suite in Williamsburg

4.98 out of 5 average rating, 268 reviews

Happy Maples!

I am a custom builder and I decided to have some fun building out my own special guest space. Welcome to Happy Maples! The suite is a private 600 sq ft hand crafted studio with private entrance, bath w/shower, large deck w/Adirondack chairs and grill, views of the gardens and 100' from the historic Mill River right behind the house. There is a queen bed and an additional twin memory foam bed available. 12 mins to Northampton, 20 mins to Amherst, Bike trail in back yard. Come for a fun visit!

Guest favorite

A darkened silhouette of trees and landscape is visible against a twilight sky. Shades of deep blue and hints of soft purple and orange create a serene backdrop, framing the natural scenery within a rounded arch.

Guest suite in Easthampton

4.92 out of 5 average rating, 268 reviews

The Floating Library: private hiker's hideaway

Spacious enough for a small family, cozy enough for a couple, a perfect alternative to a hotel, for exploring New England, or holing up to finish that book (reading or writing). TFL is a welcoming, above the garage in-law suite with a private entrance, full kitchen, full bath, laundry room, and lots of magical touches that will make your stay comfortable, unique and memorable. The location is right at the foot the hiking trails of Mt. Tom, a 20 min walk to idyllic downtown Easthampton.

Top guest favorite

A weathered wooden barn displays the sign 'Milestone Farm,' illuminated by the soft evening light. The rustic texture of the wood is showcased, reflecting the farm's charm. Nearby elements, such as a mailbox, add context to the property’s welcoming environment.

Tiny home in Northampton

4.99 out of 5 average rating, 207 reviews

Tiny House Farm Retreat: Mountain Views, Fire pit

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Top guest favorite

A peaceful backyard is depicted, featuring raised garden beds filled with various plants and flowers. A table with chairs is positioned on the grass under the shade of fruit trees, creating a serene outdoor seating area. Greenery dominates the landscape.

Apartment in Northampton

4.98 out of 5 average rating, 368 reviews

Light filled three bedroom apartment DT Florence!

Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

Top guest favorite

The image showcases a serene river scene with colorful autumn foliage framing the landscape. In the background, charming buildings with warm hues line the waterfront, while the calm water reflects the vibrant colors of the trees. Gentle hills rise in the distance.

Apartment in Conway

4.95 out of 5 average rating, 169 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, 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.

Top guest favorite

A small outdoor balcony features a metal dining table with two matching chairs, positioned on a patterned rug. A potted plant rests at the center of the table, with a view of greenery and the street visible beyond the railing.

Apartment in Northampton

4.97 out of 5 average rating, 259 reviews

Downtown updated 1 bedroom apartment w/fireplace

Feel at home in this newly updated one bedroom apartment right on the edge of the downtown district. This second floor apartment features a well-equipped kitchen, comfortable living room with working fireplace, full sized dining table, work space with wifi, large bedroom with king bed and reading chair and on-site laundry/parking. A .6 Mile walk/drive to Smith College and a five minute walk to Main St. in Northampton make this location ideal. Easy to I-91, too!

Top guest favorite

The entrance features a welcoming porch with a black bench positioned next to vibrant greenery. A climbing plant is showcased in a white pot, while colorful flowers border the stone pathway leading to the front door, which is framed by classic blue shutters.

Apartment in Northampton

4.99 out of 5 average rating, 163 reviews

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.

Guest favorite

A spacious bedroom features a queen bed with brown bedding and a day bed adjacent. Natural light streams through large windows, illuminating the hardwood floor. A woven area rug adds texture, while a dresser and a small seating area contribute to the inviting design.

Apartment in Northampton

4.87 out of 5 average rating, 407 reviews

Large Quirky Sunny Farmhouse Apartment

The apartment is spacious, bright, and sunny. Full of charming and quirky old details like original windows, hardwood floors, and not many right angles. Definitely not a vanilla box. The furnishings are clean and comfortable and go with the farmhouse feel. Please note that the private staircase used to access the apartment is original to the house. It is steep by contemporary standards and the tread depths are all a little wonky.

Top guest favorite

A metal bridge is showcased with exposed beams and a wooden walkway. The structure is surrounded by lush greenery, with trees visible in the background. Clear blue skies above create a bright and open atmosphere, inviting exploration.

Apartment in Northampton

5 out of 5 average rating, 108 reviews

Charming retro retreat with vintage soaking tub

Pet-friendly 2-bedroom apartment at the end of a quiet dead-end street close to the bike path. Stroll into downtown Northampton in just 15 minutes. Or take a 1 mile drive or bike ride to Smith College. Thoughtfully decorated with retro & contemporary details, local artwork, and a full kitchen, featuring two comfortable queen beds and a deep clawfoot tub for relaxation. A safe and serene retreat with quick access to everything.