
Holiday rentals in Hampshire County
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Top-rated holiday rentals in Hampshire County
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

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.

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.

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.

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.

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.

The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

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.

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.

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.

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!

Amherst Get-a-way retreat
Kick back and relax in this calm, stylish space. This cozy two bedroom apartment is a quick drive to down town Amherst and the 5 colleges. Peaceful setting with all the comforts of home. View birds and wildlife from the private back deck. Wifi, Roku TV, coffee and tea provided. Walking distance from a few restaurants and short drive to many others.
Popular amenities for Hampshire County holiday rentals
Other great holiday rentals in Hampshire County

Cozy get-away!

Short walk to town, 1894 house.

Modern Comfort Meets Northampton’s Vibrant Charm

Mill River Cottage (pet friendly!)

hope house

Happy Maples!

2 bedroom apartment in the heart of Noho

Beautiful 18th Century Farmhouse
Destinations to explore
- Rentals with pools Hampshire County
- Family-friendly rentals Hampshire County
- Rentals with a hot tub Hampshire County
- Guest house rentals Hampshire County
- Rentals with lake access Hampshire County
- House rentals Hampshire County
- Pet-friendly rentals Hampshire County
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Flat rentals Hampshire County
- Rentals with beach access Hampshire County
- Private suite rentals Hampshire County
- Rentals with a kayak Hampshire County
- 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





