
Places to stay near Jiminy Peak Mountain Resort
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Top-rated vacation rentals near Jiminy Peak Mountain Resort
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Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

The House of Pi
Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

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.

HEAVEN ON EARTH - Hudson Riverfront Home
Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Cantabile life in the Berkshires
Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Cozy apartment near Jiminy Peak
Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Beautiful Jiminy Peak Townhome Family Friendly
Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Berkshire Getaway Ranch 3 acres + saltwater pool
Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Beautiful Victorian. The heart of the Berkshires.
The whole group will enjoy easy access to everything from this centrally located place. The house has been completely renovated. The side patio has plenty of room for a large group with a brand new Weber grill and propane fire pit. Enjoy morning coffee on the front porch. Just steps from the Ashuwillicook Rail Trail. Greylock Glen is less than a half mile away with hiking trails. Mass MoCA is 5 miles away. This Victorian beauty is cozy, warm, and inviting.

Newly Renovated Red Door Annex
Private keypad entrance with parking. Large bedroom with a new Queen bed, full bathroom. There is a small table for dining and working, a small fridge, microwave, toaster oven, and pour-over coffee and tea in a nook outside the bedroom. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. Fire Pit. The Annex is attached to the main house but is completely private.
Popular amenities for vacation rentals near Jiminy Peak Mountain Resort
Condo rentals with wifi

Beautiful condo 2.5 miles from Mount Snow

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Spacious 3 bedroom apt in Lenox historic downtown

Flowers & Falls Spot House

Jiminy Peak Apartment

Elegant, spacious studio apt in historic mansion

Jiminy Peak Country Inn 1 Bedroom Suite

Jiminy Peak Country Inn - ski in/out condo MT view
Family-friendly house rentals

Quality, Comfort, Charm in Williamstown Center

Hudson River Sunset Getaway

19th c. Barn in The Berkshires

Brooksong, the perfect Berkshires getaway

Rustic Swedish Barn/Featured in Airbnb Magazine

Family Lodge at Jiminy Peak - Pools & Adventure

New & Cozy~Near MoCa~Deck~River

Tranquil mid-century modern Berkshires retreat
Apartment rentals with air conditioning

Charming Art Filled Apartment

Serene Suite: Hudson & Berkshires, Walk to Brewery

Romantic Warren St Penthouse w/Catskill Mtn Views

Suite 23 - Spacious Sunny 2-BR with Mountain view

The Beer Diviner Brewery Apartment

Sunny carriage house apartment

Whiteley Hideaway- walk to Mass MoCA and Downtown

Zachariah House Main St. Ashfield
Other great vacation rentals near Jiminy Peak Mountain Resort

Mountainside Condo Ski on/off

Cozy cottage on peaceful pond

Ski-In Ski-Out Loft Lift & MT. Views

Secluded cabin with babbling brook

Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

Jiminy Peak Slopeside Getaway • Ski & Adventure

Summer Mountain Retreat + Views, Fire Pit, Hot Tub

Rustic Cabin with Wood Fireplace
Destinations to explore
- Rentals with a patio Jiminy Peak Mountain Resort
- Apartment rentals Jiminy Peak Mountain Resort
- Rentals with outdoor seating Jiminy Peak Mountain Resort
- Fitness-friendly rentals Jiminy Peak Mountain Resort
- Rentals with a hot tub Jiminy Peak Mountain Resort
- Ski-in/ski-out rentals Jiminy Peak Mountain Resort
- Rentals with a fireplace Jiminy Peak Mountain Resort
- Rentals with a sauna Jiminy Peak Mountain Resort
- Rentals with a washer and dryer Jiminy Peak Mountain Resort
- Rentals with pools Jiminy Peak Mountain Resort
- Rentals with an EV charger Jiminy Peak Mountain Resort
- Rentals with a fire pit Jiminy Peak Mountain Resort
- Villa rentals Jiminy Peak Mountain Resort
- Family-friendly rentals Jiminy Peak Mountain Resort
- Condo rentals Jiminy Peak Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Six Flags New England
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Stratton Mountain Resort
- Bash Bish Falls State Park
- Thacher State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Taconic State Park
- June Farms
- Hildene, The Lincoln Family Home
- Ski Sundown
- Hudson Chatham Winery
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Naumkeag
- National Museum of Racing and Hall of Fame
- Rensselaer Polytechnic Institute
- New York State Museum





