
Places to stay near Club Wyndham Bentley Brook
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Top-rated vacation rentals near Club Wyndham Bentley Brook
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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.
4.93 out of 5 average rating, 103 reviews
Fall Foliage Luxury Cabin & View Autumn Adventures
Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!
4.97 out of 5 average rating, 109 reviews
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!
4.95 out of 5 average rating, 277 reviews
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.
4.92 out of 5 average rating, 115 reviews
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!
4.95 out of 5 average rating, 239 reviews
The Hobbit House at June Farms
Watch June Farms on Amazon Prime Video! Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Highland cows, spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!
4.97 out of 5 average rating, 256 reviews
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.
4.82 out of 5 average rating, 214 reviews
The Beer Diviner Brewery Apartment
The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.
4.9 out of 5 average rating, 234 reviews
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.
4.83 out of 5 average rating, 109 reviews
See MoCA from your mansion+Sauna!
Large bi-level 4 bedroom apartment tucked away on a hilltop oasis above Mass MoCA (3 mins by foot). 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure). Fully private with no shared spaces + outdoor Sauna! Your stay’s proceeds allow us to host refugee/immigrant musicians pro bono year-round at @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!
4.97 out of 5 average rating, 732 reviews
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.
4.93 out of 5 average rating, 108 reviews
The old sawmill from 1771
The oldest house in town, fully renovated. Beautiful two-story living room with leafy, private back deck for meals outside. Kitchen with stone counters, gas cook top, and dishwasher; two bathrooms with warm floors. Floorboards upstairs a foot wide; queen size bed with view over the trees, creek and porch.
4.99 out of 5 average rating, 387 reviewsPopular amenities for vacation rentals near Club Wyndham Bentley Brook
Condo rentals with wifi

Elegant, spacious studio apt in historic mansion
4.89 out of 5 average rating, 366 reviews
Slopeside @ Seasons on Mount Snow (Ski-In/Out)
4.92 out of 5 average rating, 105 reviews
Winter Dream! The Handle Lodge at Snowtree Condos
4.99 out of 5 average rating, 136 reviews
Base of M.S. All Seasons Fun. Deck/HotT/Sauna
4.92 out of 5 average rating, 128 reviews
Walk to Mt. Snow-Spa-Summer Pool
4.86 out of 5 average rating, 146 reviews
Mt Snow Ski In/Out at Seasons
4.88 out of 5 average rating, 262 reviews
Great Amenities-Season Condo gym-sport center-pool
4.94 out of 5 average rating, 107 reviews
3 Story Condo - 5 Minutes to Mount Snow!
4.94 out of 5 average rating, 163 reviewsFamily-friendly house rentals

19th c. Barn in The Berkshires
4.85 out of 5 average rating, 229 reviews
Brooksong, the perfect Berkshires getaway
4.93 out of 5 average rating, 212 reviews
An 18th century farmhouse
4.97 out of 5 average rating, 109 reviews
GreenHouse
4.99 out of 5 average rating, 141 reviews
Net Zero home with rustic Berkshire charm
4.93 out of 5 average rating, 136 reviews
Lakefront Retreat: Fireplace, near Jiminy Peak
5.0 out of 5 average rating, 113 reviews
Hidden Oasis in the Mountains by Evergreen Home
4.97 out of 5 average rating, 157 reviews
Lake House in Averill Park, NY
4.97 out of 5 average rating, 202 reviewsApartment rentals with air conditioning

Berkshire Mountain Top Chalet
4.93 out of 5 average rating, 193 reviews
Marie's Place
4.92 out of 5 average rating, 329 reviews
Cozy 2-Bedroom Vacation Apartment
4.99 out of 5 average rating, 112 reviews
Downtown Apartment A
4.93 out of 5 average rating, 117 reviews
Downtown | Waterfront | Walk to Shops
5.0 out of 5 average rating, 171 reviews
Historical Downtown 1 Bedroom Apartment
4.96 out of 5 average rating, 118 reviews
Charming Art Filled Apartment
4.97 out of 5 average rating, 199 reviews
Cold Spring - The White Door
4.94 out of 5 average rating, 368 reviewsOther great vacation rentals near Club Wyndham Bentley Brook

The House of Pi
4.88 out of 5 average rating, 123 reviews
Beautiful timber-frame treehouse
5.0 out of 5 average rating, 123 reviews
Wildlife Lakeside Cottage; views/wildlife
4.85 out of 5 average rating, 300 reviews
Jiminy Peak Country Inn - ski in/out condo MT view
4.92 out of 5 average rating, 85 reviews
Jiminy Peak Slopeside Getaway • Ski & Adventure
5.0 out of 5 average rating, 15 reviews
Jiminy Peak Apartment
4.86 out of 5 average rating, 37 reviews
Mountainside Condo Ski on/off
4.84 out of 5 average rating, 44 reviews
Serene+Stylish Mountain Retreat
5.0 out of 5 average rating, 43 reviewsDestinations to explore
- Stratton Mountain
- Six Flags New England
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Thacher State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Hildene, The Lincoln Family Home
- Hudson Chatham Winery
- Ski Sundown
- Rensselaer Polytechnic Institute
- Bromley Mountain Ski Resort
- Saratoga Spa State Park
- Naumkeag
- University of Massachusetts Amherst
- MVP Arena
- New York State Museum





