Vacation Rentals By Owner In Hancock, MA

Showing 20 Of 163 Vacation Rentals

$722.45

Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA

Hancock, Massachusetts, United States

Welcome to Jiminy Peak Mountain Resort in the Berkshire Mountains! Our newly-renovated mountain retreat The Lazy Bear is one of only a handful of FREE-STANDING HOUSES in the exclusive Black Diamond section of Jiminy Peak. The Lazy Bear boasts a quiet location on a dead-end street and 3 levels of luxury living complete with a spacious master suite, oversized great room with a wood-burning fireplace, a large tv/game room, and spacious outdoor deck with a gas grill and 360-degree mountain views:brbr5 Bed/3 BathbrNewly renovated, free-standingbrExclusive Black Diamond, Mountainside, Jiminy PeakbrSki-in/ski-out, Private owner's entrance to the slopes directly onto Grouse Runbr360-Degree Mountain Views in Winter Monthsbr2600+sf & 3 Levels of LivingbrSpacious, light-filled Great Room with Wood Burning Indoor FireplacebrLarge, accommodating Dining AreabrChef's Kitchen w/brand new appliances and luxury cookware brLuxurious wood brLower Level Living/Game Room w/FoosballbrSeparate Ski Room Entrance/Wet Room w/Dryers brGas Cooking, Indoor & OutbrLuxurious Wool Carpeting in BedroomsbrLarge Laundry Room with Washer/DryerbrLarge Balcony w/ Slope Views and Gas GrillbrOversized, private Master BedroombrPrivate, dead-end, neighbors on only one sidebrAlarm System & Nest DoorbellbrWi-FibrTwo Smart TelevisionsbrYear-round access to the pool at The Country InnbrSummer access to tennis courtsbrSmoke & Pet-freebrSleeps up to 4 adults & 6 children, no exceptions

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Sleeps

Exceptional(16)

$229.82

/ Nightly

Apartment

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock, Massachusetts, United States

Summary:brThis is the MOST UNIQUE suite in the Berkshires, specially designed for an incredible experience. The Master Bedroom Features a King Bed, and the main room has a Queen Sofa bed for extra room. This Peaceful Suite features a luxurious massage chair, waterfall, color changing lights, Ionic Salt Diffuser, Zen Garden, and tons of surprises you just have to see. There is even a professional massage table in the closet! The King BR comes with Oil Diffuser, Sound Machine, Bamboo bedding.brbrThe Space:brThe entire place is geared toward tranquility and fun. Your suite is center mountainbrbrAll of our deluxe rental suites, apartments, and condos are very different from the standard ones offered by mountain owners. Our accommodations are fully redone, privately cleaned, and all are RIGHT ON THE MOUNTAIN! Instead of dated lodgings, experience new furnishings, in-suite perks such as Keurig machines, air fryers, board games, plentiful soft premium beddings, and of course one-of-a-kind themed getaways. You will not see any suites like these - anywhere!brbrDuring your stay you will enjoy all the amenities the Country Inn and Jiminy Peak have to offer, including a year round outdoor heated pool, hot tubs, fitness center and more. brbrJiminy Peak is the ultimate all season rental vacation resort. Summer offers great hiking and the famous Jiminy Mountain Resort Adventure Park, complete with alpine slide, mountain coaster, trampoline park, ropes course, soaring eagle and more! Winter offers the best skiing in the tri-state area, from beginners to experts. An on site ski school, mid-difficulty BLUE-GREEN and BLUE BLACK slopes, firepits, resort restaurant and bar, and night skiing are just some of the excitement Jiminy Peak Mountain Resort offers. Jiminy uses 100% renewable energy to run its snow making, allowing for expansive skiing regardless of attendance or weather. brbrWe are owners as well as guests, so every place is meticulously cared for to earn your five star review. Our properties consistently have the best ratings on all the booking channels. We promise you will LOVE your stay!brbrGuest Access:brGuests will receive a Key code for the door via email 5 days ebfore stay along with a welcome guide. There is no need to checkin at a desk for your convenience.

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Bath

Sleeps

Exceptional(6)

$563.67

/ Nightly

Condo

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

Hancock, Massachusetts, United States

Your Home Away from Home: Ski-In/Ski-Out Luxury at Jiminy PeakbrbrWelcome to our family’s cozy retreat at Jiminy Peak Ski Resort! As lifelong skiers who grew up on the trails of Jiminy, we’ve lovingly curated this deluxe one-bedroom condo to offer a warm and welcoming space for your getaway. We don’t rent our condo often, but when we do, we take pride in ensuring it feels like home for our guests. That’s why we have a wonderful housekeeper—whom we happily overpay—to ensure everything is sparkling clean and impeccably tidy when you arrive.brbrWhy You'll Love Staying Here:brSki-In/Ski-Out Access: Start and end your day right on the slopes—no shuttles, no hassle.brThoughtfully Designed Comforts: A king-sized master bedroom, a queen-sized memory foam sleeper sofa, and a fully loaded kitchen make your stay as comfortable as possible.brAttention to Detail: From the welcoming warmth of our furnishings to the meticulous care of our housekeeper, every detail is designed to exceed expectations.brResort Perks & Amenities:brHeated Outdoor Pool (open above 25°F)brIndoor & Outdoor WhirlpoolsbrExercise Room with cardio equipment, weights, and TVbrOn-Site Dining and ShoppingbrYear-Round Fun: Day and night skiing in the winter and Mountain Adventure Park in the summer.brThe Berkshires: A Four-Season DestinationbrWhen you’re not hitting the slopes, discover the charm of the Berkshires. Visit nearby cultural treasures like Tanglewood, the Norman Rockwell Museum, and Hancock Shaker Village, or simply unwind and explore the resort’s dining, shopping, and entertainment.brbrYour Space, Thoughtfully Equipped:brMaster Bedroom: King-size bed, flat-screen TV, and private bathroom entry.brLiving Room: Queen-size sleep sofa with memory foam, pull-out armchair, and flat-screen TV.brKitchen: Fully equipped with a microwave, refrigerator, stove, toaster, coffee maker, and all necessary cookware and cutlery.brBathroom: Dual vanities and separate entries for privacy.brWhy Choose Our Condo brThis isn’t just a rental—it’s our family’s special retreat. As lifelong skiers, we’ve designed this condo to reflect our love of Jiminy Peak, and we’re committed to sharing that experience with our guests. From the unbeatable ski-in/ski-out location to the care and attention from our exceptional housekeeper, every aspect of your stay is curated for comfort, cleanliness, and convenience.brbrBook your stay now and experience the warmth, adventure, and relaxation of Jiminy Peak. Let our home become your home on the slopes!brbrbrbrbrbrbr

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Select Dates for Price

Hotel Resort

Bentley Brook at Jiminy Peak ^ Studio

Hancock, Massachusetts, United States

Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking, horseback riding, Tanglewood concerts and brilliant foliage. Then return to your beautiful resort, filled with delightful amenities and activities.brbrEXPERIENCE THE BERKSHIRESbrbrFeel the rush when you hit the slopes in this powdered wonderland.brbrReconnect with nature, break away from the daily grind and renew your perspective with a mountain escape.brbrThese resort condos are so much more than a place to lay your head at night. You have your choice of spacious accommodations in a variety of floor plans.brbrPlus, you’ll delight in the luxury of all the comforts of home. Many suites have the following great features:brbrSpacious living rooms with large-screen TV, DVD player and even video game systemsbrbrWireless Internet access to keep you connectedbrbrFully equipped kitchens with large refrigerator, stove, microwave, coffee maker — and even wine glasses!brbrAmenities:brbrIndoor Swimming PoolbrbrOrganized Activities ProgrambrbrExercise EquipmentbrbrDownhill SkiingbrbrPicnic/BBQ AreabrbrHikingbrbrSaunabrbrOutdoor Swimming Poolbrbr3 Tennis Courtsbrbr1 Indoor & 2 Outdoor Hot TubsbrbrGame RoombrbrSnowboardingbrbrLaundry FacilitiesbrbrSome amenities are available at an additional charge.brbr01. Reservations must be in the name of someone at least 21 years of age (proper photo ID must be shown at check-in). Other guests need not be at least 21 years of age.brbr02. After booking, the name(s) (up to two) and addresses of who will be checking in must be provided prior to the guest's arrival.brbr03. Failure to provide reservation name(s) may result in the guest not being able to check-in when the guest arrives at the property.brbr04. Check-in / Check-out: 4 PM / 10 AM (unless otherwise specified)brbr05. A credit card pre-authorization or cash deposit will be required upon check-in.brbr06. Suites are assigned at check-in so location within the resort varies. We can have the reservation annotated for your preference and the resort staff will do their best to accommodate based on location availability.brbr07. We are not responsible for limited or no access to amenities due to government regulations, resort policy, discontinuation or maintenance.brbr08. Late Arrivals: Please notify the resort of your late arrival and check-in no later than 48 hours after your scheduled arrival date. Failure to do so may result in the cancellation of your reservation without notification.brbr09. Your safety is very important to us, so we closely follow local regulations for maximum occupancy per unit.brbr10. Out of respect for all our guests, pets are not permitted. Please feel free to contact the resort prior to your arrival so that we may assist you in locating a local boarding facility.brbr11. Service animals that are trained to work or perform tasks for the benefit of an individual with a disability are welcome at all affiliated locations.brbr12. No smoking is allowed in the suite. Failure to comply may result in a fine.brbr13. Attending a seminar or presentation is not required as part of the booking. If you are made an offer to attend, you are under no obligation to do so. Attending a seminar or presentation is the sole choice of the renter, if offered.brbrRev: 2.5

Bath

Sleeps

Exceptional(6)

$229.82

/ Nightly

Apartment

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock, Massachusetts, United States

Summary:brWelcome to the Woodlands. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn. 1st Floor, mountain views, private parking in gated lot on Jiminy. brbrNo detail was missed in this adorable 1BR 1 BA Suite which Sleeps 4 comfortably with its King Bed and Pull out Queen Sofa in main room along with Kitchenette and Full Bath. Located in the BEST location At Jiminy - The Country Inn at the base of the mountain, you need to see this suite to believe it.brbrThe Space:brThe most unique Suite in the Berkshires - This gorgeous woodland Themed Hotel Room will bring forest magic to your summer retreat or Ski Getaway. No detail was missed in this adorable 1BR 1 BA Suite which Sleeps 4 comfortably with its King Bed and Pull out Queen Sofa in main room along with Kitchenette and Full Bath. Located in the BEST location At Jiminy - The Country Inn at the base of the mountain, you need to see this suite to believe it. Fully redone, in super desirable Building One, with private gated parking and stunning mountain viewsbrbrAll of our deluxe rental suites, apartments, and condos are very different from the standard ones offered by mountain owners. Our accommodations are fully redone, privately cleaned, and all are RIGHT ON THE MOUNTAIN! Instead of dated lodgings, experience new furnishings, in-suite perks such as Keurig machines, air fryers, board games, plentiful soft premium beddings, and of course one-of-a-kind themed getaways. You will not see any suites like these - anywhere. Even the bathroom even comes with organic washes shampoos and conditioners. brbrDuring your stay you will enjoy all the amenities the Country Inn and Jiminy Peak have to offer, including a year round outdoor heated pool, hot tubs, fitness center and more. brbrJiminy Peak is the ultimate all season rental vacation resort. Summer offers great hiking and the famous Jiminy Mountain Resort Adventure Park, complete with alpine slide, mountain coaster, trampoline park, ropes course, soaring eagle and more! Winter offers the best skiing in the tri-state area, from beginners to experts. An on site ski school, mid-difficulty BLUE-GREEN and BLUE BLACK slopes, firepits, resort restaurant and bar, and night skiing are just some of the excitement Jiminy Peak Mountain Resort offers. Jiminy uses 100% renewable energy to run its snow making, allowing for expansive skiing regardless of attendance or weather. brbrWe are owners as well as guests, so every place is meticulously cared for to earn your five star review. Our properties consistently have the best ratings on all the booking channels. We promise you will LOVE your stay!brbrGuest Access:brGuests will receive 5 days before check in access code to the keypad on the door.brbrThe Neighborhood:brLanesboro , Pittsfield, North Adams are moments away.. with all your modern amenities

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Bath

Sleeps

Exceptional(3)

$229.82

/ Nightly

Apartment

Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain

Hancock, Massachusetts, United States

Summary:brWelcome to the Jurassic Era! This is the most epic suite in all of the Berkshires! Brand new, you will love all the intricate details. From the Dinosaur Containment Chamber to fossils, to of course Giant Dinosaurs, no details are left out. It is our pleasure to bring the magic of dinosaurs to your all year retreat! Note: The room is Brand New, and will be the most epic immersive Suite in the BerkshiresbrbrThe Space:brBut more than the most amazing suite ever that will make you an instant superstar to your little dinosaur explorer, this suite is amazing. You want to pop out of bed, walk outside, and be right on the mountain - this is the place for you. This 1BR, 1BA Suite w Mountain Views features a king bed in the master bedroom that sleeps two, plus a second fold out queen sofa bed in the living room which sleeps an additional two. The Kitchenette comes complete with Keurig, Toaster, pots, pans, etc. The unit is equipped with games for those nights in, along w two TVs. As a guest, you have full use of all of Jiminy and the Inn, including yr round heated pool hot tub sauna, fitness center and morebrbrAnd of course, dinosaur themed games, decor, bedding, furnishings - Its all their to have fun exploring the room as much as Jiminy.brbrAll of our deluxe rental suites, apartments, and condos are very different from the standard ones offered by mountain owners. Our accommodations are fully redone, privately cleaned, and all are RIGHT ON THE MOUNTAIN! You get all the benefits of the Country Inn, but full reimagined in Deluxe accommodations. Lavish in n-suite perks such as Keurig machines, air fryers, Dino-themed board games, plentiful soft premium beddings, and of course a one-of-a-kind DINOSAURS getaways. You will not see any suites like these - anywhere!brbrDuring your stay you will enjoy all the amenities the Country Inn and Jiminy Peak have to offer, including a year round outdoor heated pool, hot tubs, fitness center and more. brbrJiminy Peak is the ultimate all season rental vacation resort. Summer offers great hiking and the famous Jiminy Mountain Resort Adventure Park, complete with alpine slide, mountain coaster, trampoline park, ropes course, soaring eagle and more! Winter offers the best skiing in the tri-state area, from beginners to experts. An on site ski school, mid-difficulty BLUE-GREEN and BLUE BLACK slopes, firepits, resort restaurant and bar, and night skiing are just some of the excitement Jiminy Peak Mountain Resort offers. Jiminy uses 100% renewable energy to run its snow making, allowing for expansive skiing regardless of attendance or weather. brbrWe are owners as well as guests, so every place is meticulously cared for to earn your five star review. Our properties consistently have the best ratings on all the booking channels. We promise you will LOVE your stay!brbrGuest Access:brThere is a keypad on the door so no need to carry a key. A code will be set for the duration of your stay, so you can go in and out as you pleasebrbrThe Neighborhood:brThe Country Inn at Jiminy Peak is a few miles from Pittsfield and Lanesboro, with lots of restaurants, theaters, shopping, and essentials.

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Sleeps

Exceptional(1)

$602.25

/ Nightly

Hotel Resort

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl

Hancock, Massachusetts, United States

At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipment rental just a few feet away, a winter wonderland for all ages. The area delivers a wealth of adventure making this the perfect home base for exploring Berkshire County attractions; mountainside rollercoasters and ropes courses to play on during the summer months there’s always something to do. After a day at play come back and enjoy one of the hot tubs or relax by the pool.

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Bath

Sleeps

Exceptional(16)

$680.32

/ Nightly

Condo

Ski on ski off 1 Br loft condo in the village center with private gated parking

Hancock, Massachusetts, United States

Completely remodeled 1 Br loft condo with pull out sleeper sofa located steps from everything Jiminy has to offer.Unit features wood burning fireplace,washer dryer,granite counter tops,SS appliances !

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Bath

Sleeps

Exceptional(49)

$295.09

/ Nightly

Condo

Ski season is here!

Hancock, Massachusetts, United States

Clean and bright, this updated unit is located in the heart of Jiminy and offers impeccable comfort and convenience. Park in the owner’s lot just a few steps away from the unit entrance. brbrA fully furnished kitchen and brand new smart TVs ensure you feel at home while an open space keeps you in the midst of the action. Relax in the tub or chill on the porch with a favorite beverage and people watch. brbrAdditional amenities include a full size washer and dryer, dishwasher, king size bed in one bedroom, 2 sets of bunk beds in the other. Sit by the fire playing games with family and friends or just relax on the couch after a busy day. brbrVisit www.jiminypeak.com to see all the mountain and surrounding area has to offer in all seasons! If you’re a golfer, Donnybrookgolf.com is literally just down the road. brbrCome enjoy. There is so much to do, you’ll love it here!

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Sleeps

Exceptional(3)

$767.57

/ Nightly

Private Vacation Home

Beautiful 4 Bedroom Townhouse in the Berkshires at Jiminy Peak Resort

Hancock, Massachusetts, United States

Located slope side at Jiminy Peak mountain resort in Hancock, MA, this townhouse offers guests 4 bedrooms, 3 bathrooms, and a prime location for a relaxing or adventurous stay in the Berkshires! Enjoy the mountain views and fresh air in this lovely townhome.

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Bath

Sleeps

Exceptional(15)

$532.02

/ Nightly

Condo

Beautiful Two Bedroom, Ski In/Out, Mountainside, Home away from Home!

Hancock, Massachusetts, United States

Jiminy Peak - This beautiful and premium condo was just renovated for the 2016 ski season. It is fully equipped with everything a family will need for the perfect Mountainside vacation. Two Bedrooms, accommodate 6+ guests with all the comforts of home. 10-foot ceilings and crown molding throughout. The master bedroom, with King size bed, flat screen TV, large closet and a view of the main Mountain just left of your private balcony. The master bath has duel sinks, jet tub, fully tiled, tastefully decorated and is brand new. Bedroom two a full over full bunk with stairs, large closet, flat panel TV & DVD player, kids movies with XBox 360 game console, toys, puzzles and games. Very large living room, with new and comfortable couch with queen pullout sofa, large TVs

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Select Dates for Price

Condo

Full Week of Ski-in,Ski-out @ Jiminy Peak Club Whyndam Bently Brook in Berkshire

Hancock, Massachusetts, United States

Full week rental only, Feb. 18 (in at 3pm) to Feb 25(check out 11am) @ Club Whyndham Bently Brook Resort @ Jiminy Peak - ski-in, ski out at base of MT. My Timeshare Unit is in the MAIN BLDG! (all the great amenities are IN this bldg = locker room AT lift, AT ski school, front desk, lobby, pool, hot tubs, exercise room, sauna, movie theater and kid's arcade.brUnit Includes: 2 bedrooms, sleeps 8, 2 bath (2 showers and 1 jacuzzi tub), full kitchen, washer/dryer, 3 TVs, DVD, free WIFI.brGo to Jiminypeak.com for full ski info and passes. For Hotel pictures & info go to Bentley Brook Resort website, https://www.extraholidays.com/hancock-massachusetts/wyndham-bentley-brook.aspx Resort phone # 413-738-8600.

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Sleeps

Exceptional(24)

$186.49

/ Nightly

Apart-hotel

Mountainside Condo Ski In Ski Out

Hancock, Massachusetts, United States

Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Just a short walk back to your vacation home to relax before heading to dinner at one of our on site restaurants. Jiminy offers all that you need in a resort experience – lodging, dining, shopping and an array of activities and entertainment.brbrThe space:brA privately owned unit at the base of Jiminy Peak. This unit is located on the top floor nestled away with only one adjacent neighbor. Yes, so no need to worry about any noisy visitors above your head. This unit offers unique amenities such as a boot dryer, games and movies, HD cable, high speed internet, Keurig machine, extra clean linen, stainless steel pots and dishes for cooking and basic cleaning hygiene products. A locker room is at the end of the hall to secure your equipment (key provided). The locker contains two pairs of skis and extra poles along with other gear that can be used at leisure by guests. The resort offers a year-round heated pool, 2 hot tubs, a gym, sauna, fireplace lounge and restaurants. Come enjoy the mountain!brbrGuest access:brPlease check in at the Front Desk of the Country Inn. 37 Corey Rd. Hancock, MA. Check in time is 3pm. Must be 21 or older!brbrOther things to note:brAmong the many things you will enjoy at our Resort, you will never be charged for a cleaning fee or a service fee. If you would like the apartment cleaned or clean linens delivered during your stay that can be arranged through the front desk.br

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Bath

Sleeps

Exceptional(6)

$302.8

/ Nightly

Cabin

Private Berkshire Cabin on 27acres near Jiminy Peak.

Hancock, Massachusetts, United States

Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Lenox, Hancock Shaker Village, Tanglewood, and MassMOCA.Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home cooked meals. Living room and dining room offer an open floor plan perfect for entertaining. Large deck complete with gas grill and table/chairs is perfect for outdoor entertainment. Table tennis and foos ball table in basement (Note: limited heat in basement). Rounding out the indoor entertainment options include a full assortment of adult and children board games. Outside you will enjoy 27 acres of wooded privacy complete with sledding hill, hiking trails, a stream, and pond. Every season brings new opportunities with winter sledding, spring fishing, summer strolls in the stream, and fall hiking capped off with smores by the fire pit, all completely available without leaving the property. After exploring all the on-site activities, Jiminy Peak mountain resort is only 2 1/2 miles away, offering all-season fun and dining options. Williamstown, home to Williams College and a variety of shops and restaurants, is only fifteen minutes away. Central location is ideal for exploring all the Berkshires has to offer, including museums, art galleries, and concerts. If you are looking to unplug and relax with family and friends, while exploring the vast cultural and recreation opportunities available throughout the Berkshires, this home is the place for you.

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Sleeps

Exceptional(7)

$382.49

/ Nightly

Condo

Pres day weekend! STUDIO Sleeps 4 Ski in/out Wyndham Bentley Brook JIminy

Hancock, Massachusetts, United States

I pre-reserved President and MLK weekend Friday to Monday for your family. Luxury Room is right on Jiminy Peak's learning/beginner slope. It's lift brings you to the main lift. Easy walk to restaurants and ski rentals. Excellent location. No car required. Full kitchen with all supplies. Washer/dryer in unit. Huge hot tub. Indoor pool and game room. Exact unit will vary, but will be a studio, sleeps 4

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Bath

Sleeps

Exceptional(37)

$291.82

/ Nightly

Condo

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

Hancock, Massachusetts, United States

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 Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall. Experience all the Berkshires have to offer with swimming, boating, and water skiing on nearby Pontoosuc Lake, Donnybrook Country Club with 18-hole golf course open to all, historic Lenox and Stockbridge, Tanglewood, summer stock theater festivals, and more. This three bedroom, two bath unit with porch overlooking the mountain sleeps ten and is perfect for one large family, two families, or three couples. Large, fully equipped kitchen has everything you need to make your stay easy. Enjoy panoramic views of the slopes as you relax by the cozy electric fireplace. 3 pools are a quick three minute walk away. Pool, jacuzzi, spa access, and fitness center year-round. Two additional pools to choose from late spring to early fall. Your Premier Host, Colin, will ensure that you have a wonderful stay and a great experience while in the beautifully scenic Berkshires.

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Bath

Sleeps

Exceptional(3)

$383.95

/ Nightly

Condo

IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES

Hancock, Massachusetts, United States

2BEDROOM and 2 BATH CONDO. Master Bath has large whirlpool tub. also has full sized pull out couch and portable cribs available with WASHER/DRYER and FULLY STOCKED KITCHEN, TVs in each room. Large living room with dvd player and some with balconies overlooking mountains. POOL,HOT TUBS, MOVIE THEATER/ GAME ROOM/KIDS ACTIVITY. Ski lockers with SKI IN and OUT! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

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Bath

Sleeps

Exceptional(11)

$269.87

/ Nightly

Condo

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock, Massachusetts, United States

Come and enjoy this increditable country decor.brSoak up this country cottage charm while sipping your coffee or tea with the beautiful country side.brbrVacation at home with the ski slope just steps away.brThis 1BR 1BA condo features a king bed in the master bedroom, a 2nd fold out queen sofa bed is in the living room. The kitchen is complete with Keurig, Air fryer, griddle, pot & pans, etc.brThe condo includes a mini nintendo, cards, board games for the evening & rainy days. There are also 2 TV equipped w Roku for those evening NETFLIX movies. As a guest you have full use of all Jiminy Peak amenities.brRent your very own condo in the Counrty Inn at Jiminy Peak Resort. This unit is only steps away from the ski trails with amazing views.brbrSoak up this country cottage charm, sipping your coffee or tea, all while watching the birds near the little fireplace, or while watching your favorite movie on Netflix or reading the newspaper. ... So many options!

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Sleeps

$557.28

/ Nightly

Condo

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

Hancock, Massachusetts, United States

This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features an indoor and outdoor pool and a hot tub. There's also tennis courts on site. There is a full kitchen. A game room complete with a pool table offers recreational fun. A picnic area with plenty of barbecue grills is there for your use.

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Bath

Sleeps

Exceptional(39)

$711.59

/ Nightly

Private Vacation Home

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock, Massachusetts, United States

100% private free standing house with private parking and entrance. No indoor common/shared areas.brbrQuick walk thru woods to Grouse Run ski trial. Easy access for bathroom breaks/etc so no lodge needed!brbrThe house is professionally cleaned after each guest stay.brbrSelf check in with keyless locks.brbrThis house is in a fantastic location with beautiful views!! True ski in/ski out location. br Perfect house for outdoor enthusiasts and nature lovers. Take in all Jiminy and the Berkshires has to offer!!! Quick walk through the woods to ski trail (Grouse Run).brbrHigh speed fiber optic internet and TV. Ideal for remote work!brbrBig comfortable beds. Huge space. Great fireplace with fully stocked kitchen and dinning room.brbrTerrific location in winter for skiing or snowshoeing and summer months for mountain biking, hiking, ropes course, mountain coaster, alpine slide at the Jiminy Peak base. The trails are right out the side lower lever ski room door.brbrCentrally located to all Berkshire area events and attractions...Tanglewood, Great Barrington, Lenox, Six Flags, Williamstown, golf courses, horseback riding and more!brbrThe location is true ski-in ski-out and it is also a snow shoe paradise in the winter months. brbrIf you want to get away from the busy city life for a few days leaving the crowds and traffic behind this place is for you!! One of the few free-standing homes tucked up on the mountain at Jiminy. 2500 sq ft home on a dead end street, true ski-in/ski-out, 4 bedrooms, 3 full baths. brbrHighlights include:br* Ski storage room with access to trailbr* Master suite on upper level with king bed, HDTV, jetted tub and rain showerbr* Bedroom on main level with queen bed and HD Smart TVbr* Main level has full bathroom, large fully-equipped kitchen, dining room and living room with 65 HD Smart TV and full Sonos home theater system with sub.br* Lower level has 2 Bedrooms, full bathroom, living room with cozy couch, HD Smart TV, washer/dryer and ski storage room with access to the ski trial. Each bedroom has a queen and a twin over twin bunk.br* New bed linens and towels throughout.br* Wi-fibr*Tesla Universal EV charger with J1772 adapter so works with Tesla and all non-Tesla EVsbrbrNo pets allowed however, owner's dogs have stayed at the house.brbrContact us for info and availability.br

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Rent a place that suits your needs

Condo

View 62 Condo

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Sleeps

Vacation Rentals By Owner In Hancock, MA

$722.45

$229.82

$563.67

$229.82

$229.82

$602.25

$680.32

$295.09

$767.57

$532.02

$186.49

$302.8

$382.49

$291.82

$383.95

$269.87

$557.28

$711.59

Rent a place that suits your needs

Most popular vacation rentals in Hancock

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