Holiday rentals in Hampshire County

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

House Above the Hollow

A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the famed Tree House Brewery, just 10 min away. There are many sights, country roads, trails to explore, along with many varied restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

Belchertown Apartment - near UMass & 5 colleges

1 bedroom, 1 bath apartment w full kitchen in Belchertown. Private bedroom sleeps 2. Futon in living area can sleep a 3rd. Perfect location if interested in exploring Western MA or looking for a spot to stay when visiting someone attending one of the local five colleges. 20 min to Northampton, 10 min to downtown Amherst, 15 min to UMass, 7 min to the popular wedding venue The Red Barn at Hampshire College.Within 30 min of Yankee Candle, amazing hiking, Mike's Maze, & apple picking.35 min to MGM

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.

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!

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!

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.

Cozy, Private, Central 1 Bdrm, Large Yard

Half of an adorable bungalow in beautiful, private, picturesque setting. Minutes to 91, Northampton, Amherst, 5 colleges, Treehouse Brewery, Butterfly Conservatory, Historic Deerfield, Mohawk Trail… Oversized sunny bedroom with queen bed, pull-out double sofa. Living room has large sectional sofa, TV. Full kitchen, with common appliances and cookware. Bathroom with shower/tub. Vaulted ceilings throughout. Slider to private deck and large yard, all separated from owners side of house

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

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. Clawfoot tub in downstairs bath with w/d. Swimming < 1 mile away: DAR Forest (lake), Chapel Falls (waterfall). as well as Ashfield Lake. Skiing at Berkshire East (28"), and Notchview Cross Country (30"). Super fast/reliable fiber w/bakup battery. Pet (dog) fee: $150. Sorry, no cats.