
Holiday rentals in Pioneer Valley
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Pioneer Valley
Guests agree: these stays are highly rated for location, cleanliness and more.

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!
4.95 out of 5 average rating, 161 reviews
1880s balconied luxury pad, best downtown location
Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.
4.91 out of 5 average rating, 251 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!
4.98 out of 5 average rating, 312 reviews
Mountain Retreat close to Northampton & Amherst!
Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.
4.97 out of 5 average rating, 133 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.
4.98 out of 5 average rating, 308 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.
4.97 out of 5 average rating, 497 reviews
The Suprenant House
Cozy home in the 5 college area, close to downtown Amherst minutes from UMASS and Amherst College in a rural part of Town with endless scenic views. Free fast Wifi and parking. During your stay you can enjoy a fully stocked kitchen, laundry essentials, books, board games and other activities. Your hosts live directly next door to the property and available to help at any time. You will be staying next to a working farm, where there are trucks and machines working daily.
5.0 out of 5 average rating, 185 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.
4.99 out of 5 average rating, 275 reviews
2 bedroom apartment in the heart of Noho
This memorable place is anything but ordinary. Close to I91 for Easy access to Smith, UMASS, and MT. Holyoke college. Easy short walk to the Academy of Music, art galleries, shops and over 50 great restaurants. This location is perfect for guests coming to town for an event or to just get away for a fun and relaxing visit. Pet friendly so bring the four legged love ones with you! Great off leash dog park near smith.
4.83 out of 5 average rating, 272 reviews
Gorgeous Getaway
Brand-new first-floor apartment with modern styling, a king bedroom with private bath and tiled walk-in shower, a queen bedroom, a fully equipped kitchen with quartz countertops, and a cozy living room with a flameless fireplace. Just 10 to 15 minutes from the Williston Northampton School (and CLI Conservatory), and minutes from downtown Northampton, Smith College, and Cooley Dickinson Hospital.
5.0 out of 5 average rating, 164 reviews
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
Sunny Peaceful Home
This is a home-away-from-home! The space includes a full kitchen, laundry, wireless Internet, a queen-size bed, and more. Located in a safe, quiet, residential neighborhood, there is a river out back for swimming and many books and toys in the apartment if you're traveling with small children. You'll also have a beautiful view of the river from the 2nd-floor back deck!
4.93 out of 5 average rating, 711 reviewsPopular amenities for Pioneer Valley holiday rentals
Other great holiday rentals in Pioneer Valley

The cozy clubhouse
4.97 out of 5 average rating, 190 reviews
An 18th century farmhouse
4.97 out of 5 average rating, 110 reviews
Charming retro retreat with vintage soaking tub
5.0 out of 5 average rating, 157 reviews
Newly renovated Northampton getaway!
4.96 out of 5 average rating, 133 reviews
Stunning Downtown Northampton Loft Condo 2R
4.99 out of 5 average rating, 268 reviews
Historic Williams House
4.94 out of 5 average rating, 213 reviews
Beautiful 18th Century Farmhouse
5.0 out of 5 average rating, 41 reviews
The Silo | Next to UMass & open farmland/ nature
5.0 out of 5 average rating, 36 reviewsDestinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Salem Holiday rentals
- Providence Holiday rentals
- Waterfront rentals Pioneer Valley
- Bed and breakfasts Pioneer Valley
- Cabin rentals Pioneer Valley
- Pet-friendly rentals Pioneer Valley
- Apartment rentals Pioneer Valley
- Rentals with a kayak Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Flat rentals Pioneer Valley
- Rentals with pools Pioneer Valley
- House rentals Pioneer Valley
- Rentals with beach access Pioneer Valley
- Family-friendly rentals Pioneer Valley
- Rentals with lake access Pioneer Valley
- Cottage rentals Pioneer Valley
- Private suite rentals Pioneer Valley
- Hotel rooms Pioneer Valley
- Guest house rentals Pioneer Valley
- Rentals with a hot tub Pioneer Valley
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Monadnock State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- University of Connecticut
- Taconic State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Dcu Center
- Ski Sundown
- Mount Monadnock
- Clark University
- Naumkeag
- University of Massachusetts Amherst
- Norman Rockwell Museum
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Hancock Shaker Village
- Mount Holyoke College
- Naismith Memorial Basketball Hall Of Fame
- Connecticut Convention Center





