Vacation rentals with outdoor seating in Hampshire County

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

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.

Charming, updated , 3 bedroom farmhouse farm stay

Enjoy a tranquil stay on a small market farm. Winter is coming and we are midway between Berkshire East Ski Resort and the nightlife of Northampton. Plenty of great local cross country and snow shoe trails as well as snow mobile circuits and destinations. Dog-sledding! Enjoy beautiful evening skies while sitting around the fire pit. Mingle with the goats and ducks (duck eggs usually available) . Conveniently located to Northampton, Amherst, the 5 colleges, restaurants and family activity.

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.

Sweet suite, walk to town tout suite!

NOW WITH A HOT TUB!! Fully- private master bedroom suite available in a quiet neighborhood near everything in Northampton! Your own porch with a cafe table and chairs leads to your private entrance to the suite. Roomy and bright bedroom has a huge bathroom with a shower, office/ kitchenette/ eating area, and closet with fully-supplied laundry. The king bed includes a locally-made, medium-firm mattress and abundant bedding. The TV is connected by Roku to all major streaming services.

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.

Under the Hemlocks | Amherst Refined Retreat

Escape to a private bijou guest suite under the hemlocks—a refined retreat designed for recharging, relaxation, reconnecting, and quiet focus. Every detail has been thoughtfully considered with comfort, care, and rest in mind. Beyond the guest suite, the unique off-grid screened Writer's Retreat and private courtyards offer quiet moments to unplug. A slow morning, a good book, evenings around the fire, or a long soak—Under the Hemlocks invites you to rediscover the simple pleasures.

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.