Vacation rentals in Pioneer Valley

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pioneer Valley

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

0 of 0 items showing

1 of 3 pages

Guest favorite

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!

Guest favorite

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.

Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 508 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.

Guest favorite

Guest suite in Williamsburg

4.98 out of 5 average rating, 257 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

Barn in Northampton

4.96 out of 5 average rating, 545 reviews

Brookside Carriage House. Private, Great Location.

C. 1890's Carriage House. Bright & airy, 850 sq., 2nd flr. Studio. Close to "Noho" Center. Gleaming original wood floors, 12' ceiling, skylights, modern amenities w/ rustic charm. Reserved parking. 2 sleeping nooks: 1 QUEEN, 1 FULL bed & a leather couch all on the same floor. Shower, laundry, full kitchen, dining table, comfortable lounging area, & a Juliet balconey! Eclectic, spacious, private, quiet, all in a great location! Dog friendly-Contact me 1st. Stairs. No TV. Large Studio.

Guest favorite

Rental unit in Northampton

4.93 out of 5 average rating, 101 reviews

Warm & Stylish Apartment w/laundry - walk to DT

Warm and stylish 1 bedroom apartment with private garden entrance located steps from downtown Northampton. Newly refinished with a comfortable queen bed, sleeper sectional and luxury linens. It has a fully functional kitchen, bathroom, living room with a flatscreen, Roku and high-speed wifi as well as a washer/dryer in the unit-- perfect for a staycation or for a relaxed homestay for your remote work. Walk 15 mins to restaurants downtown, 20 mins to Smith College and 2 to the bike path.

Guest favorite

Rental unit in Leeds

4.98 out of 5 average rating, 136 reviews

Private Studio for a Sweet Getaway!

We offer a cozy, comfortable, studio apartment located in the heart of the Pioneer Valley right on the bike path, a walk to Look Park and easy access to hiking. We are a 10 minute drive to downtown Northampton with lots of great restaurants and music. Our proximity to Snow Farm, Smith and the other area colleges makes this an ideal overnight spot for parents in town for a brief visit, people attending area workshops and classes or for those looking to stay longer and explore the area.

Guest favorite

Rental unit in Pelham

4.99 out of 5 average rating, 144 reviews

Pelham 2nd floor Apartment

Second floor newly finished apartment that accommodates 2 guest. Well water and septic. Green by recycling and using salvage materials. Environmentally benign materials used where possible. Solar. Utilities and internet included. Raspberries and blueberries in season. 3.9 miles from UMASS and Amherst Colleges. 5.3 miles from Hampshire College. 11 miles from Mt. Holyoke and 12 miles from Smith College. NO PETS ACCEPTED! Allergy free. Don't hesitate to contact us with questions!

Guest favorite

Rental unit in Northampton

4.94 out of 5 average rating, 327 reviews

Bike Path Hideaway Near Smith, Cooley, Northampton

Modern cozy 1BR with living space, private bathroom, private driveway, screened porch, and coded door. Wooded neighborhood. Bike path along river. 5 min. drive to Look Park. 10 min. drive to Northampton. BR has luxury queen bed and single bed, AC. Cozy LR, WiFi, 55" TV, equipped kitchen with air fryer and induction hot plate. Near excellent hikes. A family lives in attached unit so there is some noise, not during sleep hours. Cats have lived here in the past. Great getaway spot!

Guest favorite

Guesthouse in Northampton

4.93 out of 5 average rating, 262 reviews

Large Studio – Walk to Town

IMPORTANT: Please read the full description about the eco-friendly policy and click the "CONTACT HOST" button, rather than making a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

Guest favorite

Rental unit in Northampton

4.98 out of 5 average rating, 685 reviews

Tree Top Suite, cozy downtown apartment

This is an entire apartment, close to downtown. It is on the third floor, so you will have to walk up two flights of stairs. Because there are dormers (peaked areas in the ceiling), especially tall people might feel a little cramped in this space. There is a king size bed in the bedroom, a living area that includes a kitchenette, dining area, seating area and a smart TV with a fire stick, and a large bathroom. Outdoor seating on the front porch is for your use only.

Guest favorite

Rental unit in Northampton

4.99 out of 5 average rating, 106 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.