Fitness-friendly vacation rentals in Berkshire County

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Stylish 1BR, 1BA suite with an additional Pull Out Queen sleeps 4 comfortably. It sits RIGHT in the Thatcher Building in front of the MAIN ski lift in Village Center. You can not get better than that! All the convenience without the bustle. This large 650 sq ft condo features brand new decor meticulously maintained, and includes a full kitchen with all the amenities. As a guest, you will

Berkshires Family Oasis with Hot Tub, Patio, Gym

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

Serene 3-BR Berkshires Log Cabin

This spacious and comfortable 3- BR log cabin is the perfect refuge to gather with family and friends. Set on a private 60 acre lot in Becket, MA, the lodge is an inviting retreat; secluded and private in the woods, but close to all the Berkshires has to offer. There are 3 bedrooms, 1 of which has an attached full bath while the other 2 have attached half baths. There is another separate full bath on the main floor and additional half bath with infrared sauna lower level. The main floor feature

Lux on the River near Tanglewood w/220v EV charge

Relax with the entire family in this beautiful new home built on the Farmington River. Enjoy luxurious, natural open spaces with fireplace, full size kitchen 2 brms, walk out deck and so much to explore Within short distances enjoy entertainment to Tanglewood, Jacobs Pillow, Becket for Arts. Enjoy family friendly outdoor activities such as hiking at the Colebrook Reservoir or Kayaking on the Otis Reservoir. Don't forget about Fall Foliage and snow skiing. We are located for all diversities.

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Serene+Stylish Mountain Retreat

Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

Charming Country House with a Hot Tub

Nested in the southern Berkshire County, this private house is perfect for all seasons. It's a 15 minute drive from Great Barrington as well as skiing, swimming lakes, trails and tons of nature. Set on a secluded 2-acre lot, the house offers ample outdoor space with a hot tub that runs all year, a firepit and out door dining area. The house features an open kitchen and dining area, a spacious and well-appointed living room with a gas fireplace, kids play area, a garage with EV charging.

Bougie B’s Mountainside Getaway

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

Berkshire Getaway~ No Pet Fee! Walk to Distillery

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within steps of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to great hiking, skiing, antiquing & more Seasonal Hot Tub is not available until further notice, sorry for the inconvenience.

Spacious Lenox Farmhouse | Perfect Winter Getaway

Welcome to Green Garden! This charming 3 bedroom, 2.5 bathroom New England farmhouse is your cozy winter retreat in the Berkshires. After a day of skiing, exploring Lenox, or walking snowy trails, warm up by the fire pit or relax inside. Minutes from Tanglewood and downtown Lenox, you’ll enjoy winter markets, great dining, and peaceful star filled nights. Kid friendly with a Pack ’n Play, Tripp Trapp high chair, and Inglesina Fast Table chair.

Hidden Oasis in the Mountains by Evergreen Home

7 MINUTES TO BOUSQUET MOUNTAIN Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.