Family-friendly vacation rentals in Western Massachusetts

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

The Lodge on Warner Hill

On your journey to our lodge, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dead-end dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located less than 10 minutes from Berkshire East and the Deerfield River

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.

Treehouse Haven in Putney-All Seasons

Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting toilet ☽ Tea & local coffee ☽ Hot outdoor shower ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Visit for romance, time with the family, a retreat from the business of life, or even a remote work sanctuary.

Serene 1-br suite on 65 acre horse property

Enjoy nature while staying in a quiet 1 bedroom attached suite on a 65 acre horse property with it's own nature trails. It includes a private entrance with a dedicated workspace with free high-speed WiFi. Remote workers are welcome! We have up to 20 horses on the property. You will have front row viewing to several right out your windows! It's set back in the woods about a 1/3 of a mile, however it is a convenient location close to Amherst, Hampshire, UMass, Smith and Mt. Holyoke.

Artsy Pine Cabin in the Woods

Come relax in our private and cozy one room cabin tucked in the woods on the family homestead. A peaceful location for connecting with nature, writing & hiking. It's a 12'x16' cabin, with a comfortable queen size bed, electricity, mini refrigerator and electric kettle. Water is provided. Equipped with a clean outhouse and an outdoor hot shower on side of main house. ( May use indoor shower in main house in cooler months) Excellent spot for star gazing.

Hill-Ross Guest Suite

You'll have the Guest Suite at The Historic Hill-Ross Homestead with private entrance all to yourself. Guest Suite is the renovated carriage house ell off the main farmhouse which houses 2 bedrooms, 1 kitchen, 1 living room and 1 bathroom including your own private patio. One bedroom has a queen bed and second bedroom has a full bed and a single bunk bed. Hill Ross Homestead is a short, 5 minute walk into downtown Florence.

Hilltown Cabin Hideaway: A River Runs Through It!

Rediscover peace in the Hilltowns of Western Mass. Charming 3BR cabin in nature, with full kitchen, bath, laundry, TV and Wifi! Relax in a serene, wild and beautiful place. Cook a meal with friends. Take a riverside hike, or explore an Old Growth Forest nearby. Go fishing. Watch fireflies. Jump in a swimming hole. Lie in the meadow. Watch the clouds. Enjoy the Hot Tub for two. *Breath the free air again!*