Smoking-friendly holiday rentals in Western Massachusetts

Country Guest Cottage/Barn

Enjoy nature in the guest cottage/barn on our property in bucolic Litchfield County. King bed in the sleeping loft and queen bed in the room. Air mattress available. Nestled in the Litchfield Hills three miles from Lake Waramaug and close to the quaint shops, restaurants, galleries and cultural scene in Kent, Bantam, Litchfield, Washington, New Preston and Cornwall, among others. Hike beautiful Kent Falls and explore the many hiking trails and ponds, lakes and rivers. Newly upgraded with Wi-Fi!

The Mushroom Palace (Hot Tub, Sauna & Cold Plunge)

This isn't your typical bougie & hip upstate Airbnb, it's definitely not too modern and it definitely ain't the prettiest but it's got some soul and dope vibes. This was the first property I bought when I moved upstate and me, my dog and roommates lived here for years before I started renting it! It's a great space for an affordable getaway for a couple (with your pet!) or for a group of homies. Centrally located within 10 mins to Woodstock, Hunter, Saugerties, Kingston, etc - come relax <3

Runamuk Farm camp with a view!

Picturesque location on farmland with views of the mountains. We are a micro farm. Wake up and watch the sunrise and go for a short hike on the property, and get to know the animals. We are located 35 minutes from Saratoga Springs and Lake George, NY and 45 minutes from Dorset and Manchester, VT. Hike the Adirondack or Green Mountains, paddle the streams or go to a nearby small city for a play, a festival, or a concert. There is a long list of things to do and see within an hour of our camp.

Get Away Rock Farm Suite UConn Best Rated Clean

The Get Away Studio Suite on Rock Farm” is a quiet, safe, airy 600 sf open floor plan with 9ft ceilings. Peaceful secluded country setting 600ft in woods. Enjoy the comfy king bed, twin bed, kitchen, dining, living area & full bath. All Sundries & amenities. DIY breakfast on us! Near malls, shopping, lakes, 13 min UCONN, 20 min Hartford, trails & parks only mins away. WE ARE 5 ⭐️ RATED CLEAN with excellent hospitality. Need more space? See The Hide Away https://www.airbnb.com/h/atrockfarm

Treehouse compound, no cleaning fee

The rental includes both treehouses (toilet in each), cooking/eating pavilion (only cold water at sink) (outhouse nearby), outside shower (cold), firepit. Additional guests above the 2 included in per night stay are $30 per person per night up to a maximum of 11 guests during the warmer months and 5 guests total during the cooler ends of the season (June and mid Sept to mid Oct). Beds: 3 doubles, 5 singles. No pets allowed. Not ideal for very young children or people with mobility issues.

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

The Stone Cottage Close to HITS

In the 1700s Queen Anne of the Netherlands gifted a parcel of land to her Dutch subjects, the Schoonemakers. The family built a stone cottage, from which they cultivated acres of orchards in the Hudson Valley. Today, you can stay in this 275-year old stone cottage and enjoy its modern kitchen, European bath, wide-plank pine floors and sun lit bedrooms. Half a mile away, you'll find Falling Waters preserve with hiking trails through the woods and down to the Hudson River.

An Adirondack Tree House Retreat

Our treehouse is one of the most sought after places for couples to reconnect with nature. Nestled in the foothills of the Adirondack Mtns. and just 9 miles from Saratoga Springs NY, boasting quiet solitude. The winding staircase leads to a sleeping area and covered porch. Also, outdoor kitchen, deck, fire pit and full bath just a few steps away. Please keep in mind that our treehouse is meant as a quiet retreat for 1-3 people.