Smoking-friendly holiday rentals in The Berkshires

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

The Black Dymond A Private Streamside Cabin

A 2.5 hour drive from NYC to a serene, private, woodland, streamside home. This cabin sits on the very edge of the Catskill Mountains. It's cozy, modern, and minimalistic with a touch of rustic elegance. All new appliances with all the cooking necessities, a comfortable bed with large screen smart tv, excellent wifi service, a romantic gas-powered fireplace and the most private back deck away from the world to get lost for a weekend in the beauty of the woods.*Now offering mid-week price deals!

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

Hot Tub, Fire Pit, Fully-Fenced Yard, Wood Stove

Pet friendly, with a fully fenced in yard, The Hartwood House is the perfect upstate getaway. Located in beautiful West Saugerties, this 2 bedroom/1 bath home is designed to unwind and relax. Secluded and quiet, a central base to explore the Catskills. Just minutes to all the Woodstock/Saugerties destinations, HITS, Hunter Mountain, and more. This is a private oasis in the heart of the Catskills. Features include a hot tub, fire pit, BBQ, and more to make experience one you'll never forget!

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

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.

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 a comfy king bed, twin bed, kitchen, dining, living area & full bath. All Sundries & amenities. DIY breakfast! Near malls, groceries, lakes, 13 min UCONN, 20 min Hartford, trails & parks only mins away. WE ARE 5 ⭐️ RATED CLEAN with excellent hospitality. See The Hide Away https://www.airbnb.com/h/atrockfarm

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing pond and a deck offering panoramic resort views, it's a perfect outdoor retreat. Inside, enjoy a pool table, Pac-Man arcade, and shuffleboard for endless fun. A 2-minute drive to town makes dining and shopping convenient. The cabin's modern amenities, cozy fireplace, outdoor firepit, and hot tub guarantee a comfortable and relaxing stay.