Lanesborough Rentals
- From $175 per night (USD)
VRBO
Berkshire Village Carriage House - Super Private!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Private, unique getaway in the center of the Berkshires. We're a 3 minute walk to the Ashuwillticock rail trail. Situat ...
From $175 per night (USD)VRBO
- From $210 per night (USD)
Expedia
Wildlife Cottage by the Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Light and bright defines the newly renovated cabin boasting spectacular wood throughout and freshly decorated rooms. Ra ...
From $210 per night (USD)Expedia
- From $380 per night (USD)
VRBO
Lakeside Berkshires Home Near Hiking & Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the Berkshires for a peaceful mountain respite at this charming, rustic 3-bedroom, 2-bath lakeside home. Choos ...
From $380 per night (USD)VRBO
- From $191 per night (USD)
Expedia
Charming historic cottage on scenic road to Mt. Greylock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room scho ...
From $191 per night (USD)Expedia
- From $149 per night (USD)
VRBO
Bright Boho Apt. in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This bright 1BR/1BA is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in ...
From $149 per night (USD)VRBO
- From $129 per night (USD)
VRBO
Cozy Rustic Apt. in 18th c. Berkshire Farmhouse near Mt.Greylock & Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built ...
From $129 per night (USD)VRBO
- From $209 per night (USD)
VRBO
Hearts Desire is a furnished whole house in a small, colorful garden center.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated, one level house with 2 rooms with king sized beds, 1 queen size sleeper sofa. Fully furnished kitchen ...
From $209 per night (USD)VRBO
- From $311 per night (USD)
VRBO
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Greetings from John at the American House! This is the perfect getaway to destress and relax! This is an original Lincol ...
From $311 per night (USD)VRBO
- From $289 per night (USD)
VRBO
Mounatin Getaway in the Heart of the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Lynne Court Guesthouse in the heart of the Berkshires! We are happy to share our gorgeous, nature-surrou ...
From $289 per night (USD)VRBO
- Click For Pricing
VRBO
Available for Healthcare and long term stays welcome 3 miles from Hospital
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
If you are coming to the area to help in one of our Hospitals or Healthcare facility please contact us for booking optio ...
Click For PricingVRBO
- From $469 per night (USD)
VRBO
Berkshire Lake House vacation home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Gorgeous Summer Home located in an ideal setting, on the shore of one of the Berkshire's largest lakes! Private Waterfro ...
From $469 per night (USD)VRBO
- Click For Pricing
VRBO
Available for Winter Rental, Healthcare, Central
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
If you are coming to the area to help in one of our Hospitals or Healthcare facility please contact us for booking optio ...
Click For PricingVRBO
- From $175 per night (USD)
VRBO
Monthly\/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fully funished charming openspace house with kitchen dining and living areas, modern wood stove , contemporary master b ...
From $175 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Huge Beautiful House-2 families-16 Acres -Low rate March 3-5\/ 2 min from Jiminy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
2 MIN TO JIMINY PEAK - right down the road! Reduced rates for remaining ski weekends. Great for 2 families! Come and enj ...
From $263 per night (USD)VRBO
- From $749 per night (USD)
VRBO
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Our 6BR home is super comfortable, designed for multiple families to share (max 14 guests), up to date, and just minutes ...
From $749 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Berkshire Pontoosuc Lake Beauty-Modern Amenities On The Lake
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
This home has been 100% remodeled! With a beautiful spot directly on Lake Pontoosuc, the new kitchen, bathrooms, firepla ...
From $500 per night (USD)VRBO
- From $213 per night (USD)
VRBO
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two bedroom condo in the Mountainside area is one of the most luxurious and appealing places to stay at Jiminy Peak ...
From $213 per night (USD)VRBO
- From $283 per night (USD)
VRBO
Stylish cottage located by Pontoosuc Lake with lake views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Kick back and relax in this French influenced, stylish cottage located in one of the best Pontoosuc Lake neighborhoods t ...
From $283 per night (USD)VRBO
- Click For Pricing
VRBO
Charming A-Frame Near all the Best parts of the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our A-Frame Cabin is the perfect place to disconnect and get away from it all! A family member literally built it by han ...
Click For PricingVRBO
- From $306 per night (USD)
VRBO
Historic Stone Church in The Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Plac ...
From $306 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Wake up to spectacular sunrise lake views from the deck or while soaking in the hot tub. Close to all the year round a ...
From $550 per night (USD)VRBO
- From $1028 per night (USD)
Expedia
6-BR Country Estate 14-Min. to Jiminy Peak
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Summary: Expansive Berkshires family home situated on 4 pastoral acres. The home features a post-and-beam primary with 6 ...
From $1028 per night (USD)Expedia
- Click For Pricing
Expedia
This house is a 3 bedroom(s), 1 bathrooms, located in Lanesborough, MA.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Ski, Sun, Relax, Repeat. This gorgeous ranch home is located 13 minutes from Jiminy Peak, and 19 minutes from Bosquet Mo ...
Click For PricingExpedia
- From $129 per night (USD)
VRBO
Charming Apt. in 18th c. Berkshire Farmhouse near Mt.Greylock and Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy the Berkshires while staying in a historic farm house minutes from Jiminy Peak Ski Resort, walking distance to cof ...
From $129 per night (USD)VRBO
- From $262 per night (USD)
VRBO
Chic Berkshire Retreat by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feel like you have entered your own oasis in this charming retreat. A hidden gem set far back from the road, tucked away ...
From $262 per night (USD)VRBO
- From $576 per night (USD)
Expedia
Mountain Blossom Retreat by Evergreen Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This centrally located property at the base of Mount Greylock offers luxury and tranquility on 60 private acres with swe ...
From $576 per night (USD)Expedia
- From $633 per night (USD)
VRBO
Ray of Sunshine Berkshire Home on Pontoosuc Lake
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
BRAND NEW CONSTRUCTION! But we're not new to this market. This is our 4th home on Pontoosuc Lake. We've been successf ...
From $633 per night (USD)VRBO
- From $293 per night (USD)
VRBO
house with view in the berkshires\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the charm of this newly renovated home with a wrap-around deck with vistas of a lake and mountains. Airy ope ...
From $293 per night (USD)VRBO
- From $388 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $388 per night (USD)VRBO
- From $251 per night (USD)
Expedia
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This ski-in, ski-out condo is located right at the base of the mountain in JJ’s Lodge in the heart of the village at Jim ...
From $251 per night (USD)Expedia
- From $445 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $445 per night (USD)VRBO
- From $388 per night (USD)
Expedia
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $388 per night (USD)Expedia
- Click For Pricing
VRBO
Full Week of Ski-in,Ski-out @ Jiminy Peak Club Whyndam Bently Brook in Berkshire
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Full week rental only, Feb. 18 (in at 3pm) to Feb 25(check out 11am) @ Club Whyndham Bently Brook Resort @ Jiminy Peak ...
Click For PricingVRBO
- From $208 per night (USD)
Expedia
UNIQUE - 1BR Country Condo @ Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Come and enjoy this increditable country decor. Soak up this country cottage charm while sipping your coffee or tea with ...
From $208 per night (USD)Expedia
- From $295 per night (USD)
VRBO
Mountainside Condo @ Jiminy Peak in the Berkshires
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 6
Treat yourself and be our guest at our terrific mountainside getaway, a private condo nestled at the base of Jiminy Peak ...
From $295 per night (USD)VRBO
- From $499 per night (USD)
Expedia
Ski In & Ski Out - Deluxe 1 Bedroom Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Fantastic location at the base of Jiminy Peak Ski Resort. Fully equipped deluxe one bedroom condo with ski in and ski o ...
From $499 per night (USD)Expedia
- From $570 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $570 per night (USD)VRBO
- Click For Pricing
Expedia
IN\/OUT SKIING CONDO , POOL, MOVIE THEATER\/ KIDS ACTIVITIES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
2BEDROOM and 2 BATH CONDO. Master Bath has large whirlpool tub. also has full sized pull out couch and portable cribs a ...
Click For PricingExpedia
- From $177 per night (USD)
VRBO
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain This 1BR 1 BA Ground Floor Unit righ ...
From $177 per night (USD)VRBO
- From $613 per night (USD)
Expedia
Ski on ski off 1 Br loft condo in the village center with private gated parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Completely remodeled 1 Br loft condo with pull out sleeper sofa located steps from everything Jiminy has to offer.Unit f ...
From $613 per night (USD)Expedia
- From $84 per night (USD)
VRBO
Wyndham Bentley Brook-Ski In\/Out, Indoor + Outdoor Pools - Only 25% Deposit!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
WHAT YOU’LL LOVE: Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley B ...
From $84 per night (USD)VRBO
- From $249 per night (USD)
VRBO
Berkshires Jiminy Peak Mountainside Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful two bedroom two bath fully furnished condominium style unit at Jiminy Peak. Home away from home! Fully furnis ...
From $249 per night (USD)VRBO
- From $172 per night (USD)
VRBO
Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
*Vrbo is currently experiencing technical issues related to displaying accurate information under “Rooms & beds.” The co ...
From $172 per night (USD)VRBO
- From $249 per night (USD)
Expedia
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk outside, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charmin ...
From $249 per night (USD)Expedia
- From $159 per night (USD)
VRBO
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On\/Off at Mountain Base
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain - this is the place for you. This 1B ...
From $159 per night (USD)VRBO
- From $84 per night (USD)
VRBO
Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
WHAT YOU’LL LOVE: Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley B ...
From $84 per night (USD)VRBO
- From $509 per night (USD)
VRBO
Gorgeous 3BR 3BA Sleeps 8 Ski On \/ Off Jiminy Peak-2000 Sq Ft Mountainside Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Right on the mountain, this spacious 1900 sq. ft. retreat Condo is your home away from home. It's the best way ...
From $509 per night (USD)VRBO
- From $88 per night (USD)
Expedia
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $88 per night (USD)Expedia
- From $746 per night (USD)
VRBO
Jiminy Peak, Berskshires, MA, Luxe Living
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
5 Bed/3 Bath Newly renovated, free-standing Ski-in/ski-out, Black Diamond, Mountainside, Jiminy Peak Private owner's en ...
From $746 per night (USD)VRBO
- Click For Pricing
Expedia
2 Bedroom Deluxe - Club Wyndham Bentley Brook\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At the base of Jiminy Peak Ski Mountain, this resort is an exceptional choice for mountainside play. The area delivers a ...
Click For PricingExpedia
- From $195 per night (USD)
VRBO
Pittsfield Home w\/ Deck - 12 Mi to Jiminy Peak!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Great for outdoor enthusiasts, this 3-bedroom, 2.5-bathroom vacation rental home features a balcony, a deck, a patio, an ...
From $195 per night (USD)VRBO
- From $206 per night (USD)
Expedia
1st Floor Mountain View Suite Ski On\/Off At Jiminy- Fully Redone Decor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charm ...
From $206 per night (USD)Expedia
- From $166 per night (USD)
VRBO
Deluxe Mountain View Nautical Suite Jiminy Ski On\/Off- Fully Redone Decor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA off lobby Unit has som ...
From $166 per night (USD)VRBO
- Click For Pricing
Expedia
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This spacious one-bedroom resort suite measures approximately 780 to 880 square feet. You will enjoy two queen beds in t ...
Click For PricingExpedia
- From $529 per night (USD)
VRBO
2 Bedroom Condo, Sleeps 8, Skiing, Jiminy Peak Mountain, Bentley Brook Resort!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the m ...
From $529 per night (USD)VRBO
- From $514 per night (USD)
VRBO
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
For 2023, a massive gut reno has been completed, adding a 24ft wide sunroom overlooking the lake, 2 new bedrooms and a b ...
From $514 per night (USD)VRBO
- Click For Pricing
VRBO
2 Bedroom Deluxe Condo w\/ Full Kitchen at Bentley Brook, Jiminy Peak Ski Mount!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the m ...
Click For PricingVRBO
- From $642 per night (USD)
VRBO
Wyndham Bentley Brook Condo Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy great year round activities from white water rafting and hiking in the summer, to skiing at the famous Jiminy Peak ...
From $642 per night (USD)VRBO
- Click For Pricing
VRBO
Ski in\/out @ Jimney Peak Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 80
This is a timeshare that I booked but I am unable to use this year!! A very desirable time of year - Presidents week!! S ...
Click For PricingVRBO
- Click For Pricing
VRBO
Jiminy Peak ski in\/ski out Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Wyndham Bentley Brook. Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully e ...
Click For PricingVRBO
- From $141 per night (USD)
VRBO
Hancock, MA: Studio w\/Valley Views at All-Seasons Resort: Skiing, Hiking & More!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. S ...
From $141 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Wyndham Bentley Brook - Jiminy Peak ski in\/out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, living ...
From $400 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Berkshires Living!! Beautiful Location, Breathtaking Sunsets, Fully Reno Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy your own private summer mountaintop in the Berkshires - Two story, completely renovated air conditioned home on ...
From $250 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Bentley Brook Jiminy Peak ski in ski out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, living ...
From $800 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Wyndham Bentley Brook at Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, livin ...
From $375 per night (USD)VRBO
- Click For Pricing
VRBO
Bentley Brook ski in\/ski out at Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, livin ...
Click For PricingVRBO
- From $439 per night (USD)
VRBO
Summer in the Berkshires...Mountain Fun, Tanglewood, and more!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful three bedroom two bathroom condo is located in JJs Lodge in middle of it all. Spacious, immaculately clea ...
From $439 per night (USD)VRBO
- From $480 per night (USD)
VRBO
Wyndham Bentley Brook at Jiminy Peak ski in ski out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, living ...
From $480 per night (USD)VRBO
- From $357 per night (USD)
VRBO
Wyndham Bentley Brook Jiminy Peak ski in\/out unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, livin ...
From $357 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Comfy Suite in the Berkshires w\/ WiFi & Great Resort Amenities!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
So much, So Close - Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Sp ...
From $179 per night (USD)VRBO
- Click For Pricing
VRBO
Wyndham Bentley Brook at ski in\/ ski out Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, livin ...
Click For PricingVRBO
- From $600 per night (USD)
Expedia
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Lakefront Home for Rent. Amazing location close to skiing, hiking, restaurants, Tanglewood and everything the Berkshires ...
From $600 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Mountainside: Large 3-level Jiminy Peak Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
From our easily accessible, newly renovated, fully equipped spacious home you can walk to the ski trails, hike and explo ...
From $409 per night (USD)VRBO
- From $130 per night (USD)
VRBO
Vacation Village In The Berkshires 5 Star Resort - Suite B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gold Crown Resort! Spectacular mountain views, clubhouse, indoor pool, outdoor pool, game room, playground, kiddy pool, ...
From $130 per night (USD)VRBO
- From $743 per night (USD)
VRBO
Lakeside Home With Pool-Completely Renovated
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
On beautiful Lake Pontoosuc, this 100% renovated home is complete with a heated outdoor pool! Every detail has been att ...
From $743 per night (USD)VRBO
- From $512 per night (USD)
VRBO
Family Friendly Townhouse in the Heart of Jiminy Peak
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the Jiminy Peak Mountain Resort and explore the Berkshires during Spring, Summer, and Fall in this highly desirabl ...
From $512 per night (USD)VRBO
- From $485 per night (USD)
VRBO
Beautiful Two Bedroom, Ski In\/Out, Mountainside, Home away from Home!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Jiminy Peak - This beautiful and premium condo was just renovated for the 2016 ski season. It is fully equipped with eve ...
From $485 per night (USD)VRBO
- From $392 per night (USD)
VRBO
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 25
Welcome.....we invite you to come enjoy the great space of our beautiful home with your family and friends in our unique ...
From $392 per night (USD)VRBO
- From $723 per night (USD)
VRBO
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
100% private free standing house with private parking and entrance. No indoor common/shared areas. Quick walk thru woo ...
From $723 per night (USD)VRBO
- From $88 per night (USD)
Expedia
Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $88 per night (USD)Expedia
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VRBO
WEEKEND FUN
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
DVD Player Television Wi-Fi Internet Access Hairdryer Washer/Dryer In Unit Balcony/Patio Wyndham Bentley Brook. Locate ...
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Expedia
Ski resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Family oriented ski resort . Many amenities with activities for all age groups .No need to leave the property .Swimming ...
Click For PricingExpedia
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Expedia
Berkshire Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy 3 bedroom house features a spacious 1/2 an acre fenced in back yard with a pool and hot tub in the beautiful B ...
Click For PricingExpedia
- From $186 per night (USD)
VRBO
Springtime in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bring the whole family to this great place with lots of room for fun. Jiminy Peak in Hancock, Massachusetts offers exce ...
From $186 per night (USD)VRBO
- Click For Pricing
VRBO
VACATION VILLAGE IN THE BERKSHIRES MA-2 BDRM CONDO
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Professionally decorated in a traditional New England style, Vacation Village in the Berkshires offers spacious suites w ...
Click For PricingVRBO
- From $282 per night (USD)
Expedia
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On\/Off Country Inn Redone
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk outside, and be right on the mountain - this is the place for you. This 1BR, ...
From $282 per night (USD)Expedia
- Click For Pricing
VRBO
2 Bedroom Condo, Sleeps 8, Kitchen, Jiminy Peak Ski Mountain, Bentley Brook!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the m ...
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- From $294 per night (USD)
Expedia
Cozy couple resort style condo overlooks the beautiful Massachusetts mountains.\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A dream getaway. Perfect for a couple or family. Enjoy a late night swim and or a game of pool in the clubhouse. Wake up ...
From $294 per night (USD)Expedia
- Click For Pricing
VRBO
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Welcome to Wyndham Bentley Brook, your gateway to the ultimate ski-in, ski-out experience at the majestic Jiminy Peak! N ...
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- Click For Pricing
VRBO
Your Winter Escape: Wyndham Bentley Brook Ski-In, Ski-Out Bliss at Jiminy Peak!\"
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Experience the ultimate ski-in, ski-out getaway at Wyndham Bentley Brook, nestled in the heart of the Berkshire Mountain ...
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- Click For Pricing
VRBO
Fun on the slopes with pool @Vacation Village Berkshires1.0 miles to Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bring your family at this private unit at the Vacation Village in the Berkshires. Views of the Jiminy Peak Ski Resort sl ...
Click For PricingVRBO
- From $200 per night (USD)
Expedia
345 Cozy Stay! 1.5 Miles to Pontoosuc Lake \n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect place for those seeking peace and quiet and lovers of nature and beautiful spaces. Easy access to all things ...
From $200 per night (USD)Expedia
- From $799 per night (USD)
VRBO
Escape to Serenity: Unplug in the Berkshires!\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In our modern world, "unplugging" has never been more important. Vacation Village in the Berkshires offers the perfect l ...
From $799 per night (USD)VRBO
- From $120 per night (USD)
Expedia
Entire home in Dalton, Massachusetts, United States
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. ...
From $120 per night (USD)Expedia
- From $640 per night (USD)
VRBO
Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Located slope side at Jiminy Peak mountain resort in Hancock, MA, this townhouse offers guests 4 bedrooms, 3 bathrooms, ...
From $640 per night (USD)VRBO
- From $159 per night (USD)
Expedia
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk out your door, and be right on the mountain - this is the place for you. This ...
From $159 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Ski-In\/Ski-Out at Jiminy Peak in the Country Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Jiminy Peak Mountain Resort is the perfect Berkshire get away for skiing, mountain biking, snow shoeing, mountain coaste ...
From $150 per night (USD)VRBO
- Click For Pricing
Expedia
Bentley Brook at Jiminy Peak ^^ 2 Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski ...
Click For PricingExpedia
- Click For Pricing
VRBO
Bentley Brook at Jiminy Peak ^ Studio
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski ...
Click For PricingVRBO
- From $266 per night (USD)
Expedia
Must See Jurassic Dino Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to the Jurassic Era! This is the most epic suite in all of the Berkshires! Brand new, you will love a ...
From $266 per night (USD)Expedia