Hancock Rentals
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Hot SKI-in SKI-out Rentals Bentley Brook Resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
A stay at Bentley Brook Resort is a cozy, mountain retreat. Enjoy ski-in, ski-out access, spacious accommodations, and o ...
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Expedia
Ski Jiminy Peak Xmas wk Sun-Wed 3 nites; Ski In\/Ski Out @Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wyndham Bentley Brook - Delux 2 Bedrm/2 Bathrm fully equipped Condo. Master Bdrm has K bed with shwr & jacuzzi, while 2n ...
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Expedia
Ski Jiminy Peak Xmas wk Thurs-Sun 3 nites; Ski In\/Ski Out @Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wyndham Bentley Brook - Delux 2 Bedrm/2 Bathrm fully equipped Condo. Master Bdrm has K bed with shwr & jacuzzi, while 2n ...
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VRBO
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Wyndham Bentley Brook, a premier ski-in, ski-out resort, offers the ultimate winter escape. Enjoy the slopes and cozy ac ...
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Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipm ...
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- From $95 per night (USD)
Expedia
Private Guest Suite in 1771 Farmhouse - 5 minutes to Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Berkshires this winter in this cozy guest suite on a circa 1771 farm. Originally a summer kitchen and sto ...
From $95 per night (USD)Expedia
- From $465 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 $465 per night (USD)VRBO
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Expedia
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Bentley Brook Resort offers an unparalleled getaway at the base of Jiminy Peak. Nestled in the picturesque Berkshires, ...
Click For PricingExpedia
- From $764 per night (USD)
VRBO
Ski-In, Ski-Out Left Bank Lodge
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Welcome to the Berkshires and all that Jiminy Peak Mountain Resort has to offer. This spacious townhome has all that you ...
From $764 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 $107 per night (USD)
VRBO
Outside Adventure-Skiing, Hiking, and Relaxation
- 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 $107 per night (USD)VRBO
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Expedia
Ski resort, Wydham Bently Brook in Berkshire mountains, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At the base of Jiminy Peak Ski Mountain, this ski resort is an exceptional choice for mountainside play. The area delive ...
Click For PricingExpedia
- From $179 per night (USD)
VRBO
Gorgeous Mountain View Suite Ski On\/Off At Jiminy - Fully Redone Decor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to modern country comfort. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn ...
From $179 per night (USD)VRBO
- From $799 per night (USD)
VRBO
2 Bedroom Deluxe Condo w\/ Kitchen at Bentley Brook, Jiminy Peak Ski Mountain!!
- 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 $799 per night (USD)VRBO
- From $149 per night (USD)
VRBO
Mountainside Condo Ski In Ski Out
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Just a short walk back ...
From $149 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Luxurious & Cozy Home for Your Skiing Trip to Jiminy Peak or MASS MoCA Visit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the Ultimate Berkshires Retreat: The Berkshire Apple House 🌟 Luxurious Comfort in the Heart of Berkshires Ne ...
From $400 per night (USD)Expedia
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VRBO
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Bentley Brook Resort stands as a winter haven, providing unmatched ski-in, ski-out grandeur. Immerse yourself in the enc ...
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- From $190 per night (USD)
Expedia
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
- 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 $190 per night (USD)Expedia
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VRBO
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - B
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipm ...
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Expedia
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipm ...
Click For PricingExpedia
- From $268 per night (USD)
VRBO
Modern Rustic Cottage in the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our Modern Rustic Cottage in the Berkshires! The Accommodations: Bedroom 1: A comfortable queen-sized bed. Be ...
From $268 per night (USD)VRBO
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Expedia
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Family friendly resort with indoor/outdoor heated pool, 2 hot tubs, fitness gym, game room, ski/equip rentals, daily act ...
Click For PricingExpedia
- From $462 per night (USD)
VRBO
Comfortable Berkshires retreat on mtn resort, SISO
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a ...
From $462 per night (USD)VRBO
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Elegant Mountain View Retreat By Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Explore the best of the Berkshires at this private country retreat, minutes from the Williams campus, Jiminy Peak, world ...
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- From $519 per night (USD)
VRBO
2 Bedroom Deluxe Condo, Sleeps 8, Jiminy Peak Mountain Skiing, at 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 ...
From $519 per night (USD)VRBO
- From $539 per night (USD)
VRBO
2 Bedroom Condo, at Jiminy Peak Ski 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 $539 per night (USD)VRBO
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VRBO
2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, 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 ...
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VRBO
2 Bedroom Deluxe Condo w\/ Kitchen, at 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 $549 per night (USD)
VRBO
2 Bedroom Deluxe Condo at Jiminy Peak Ski 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 $549 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Vacation Village in the Berkshires - 1 Bedroom \n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
There’s a romantic mysticism about the Berkshires, and you can soak it all in at Vacation Village in the Berkshires. Spr ...
From $120 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Vacation Village in the Berkshires - 1 Bedroom \n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
There’s a romantic mysticism about the Berkshires, and you can soak it all in at Vacation Village in the Berkshires. Spr ...
From $120 per night (USD)VRBO
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Expedia
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in\/out
- 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
- From $275 per night (USD)
VRBO
Great Pet Friendly Condo at Jiminy Peak for Spring Skiing
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Beautiful condo at Jiminy Peak's Country Village. Two-bedroom condo with a full bath and laundry, completely renovated i ...
From $275 per night (USD)VRBO
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VRBO
Ski-in\/Ski-out - Club Wyndham Bentley Brook - Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At the base of Jiminy Peak Ski Mountain, Club Wyndham Bentley Brook offers direct access to the slopes. This 2 BR unit s ...
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- From $247 per night (USD)
VRBO
Ski season is here!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Clean and bright, this updated unit is located in the heart of Jiminy and offers impeccable comfort and convenience. Pa ...
From $247 per night (USD)VRBO
- From $799 per night (USD)
VRBO
Ski-in\/Ski-out - Club Wyndham Bentley Brook - Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At the base of Jiminy Peak Ski Mountain, Club Wyndham Bentley Brook offers direct access to the slopes. This 2 BR unit s ...
From $799 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Let this newly renovated 3-bedroom, 2-bathroom townhouse, with European finishes, sky lights and brand new kitchen, bath ...
From $350 per night (USD)VRBO
- From $500 per night (USD)
VRBO
MLK and Pres weekend available! Ski in\/out - Jiminy Peak Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
I pre-reserved the Pres and MLK weekend Fri to Monday for your family! Luxury Room is right on Jiminy Peak's learning/b ...
From $500 per night (USD)VRBO
- From $500 per night (USD)
VRBO
MLK and Pres weekend available! Ski in\/out - Jiminy Peak Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
I pre-reserved President and MLK weekend Friday to Monday for your family. Luxury Room is right on Jiminy Peak's learni ...
From $500 per night (USD)VRBO
- From $433 per night (USD)
VRBO
Wyndham Bentley Brook Condo Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Nestled in the Berkshire Mountains at the base of Jiminy Peak Ski Mountain, Wyndham Bentley Brook takes "weekend getaway ...
From $433 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Snowdrop Lodge - Beautifully Renovated Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated berkshire condo within Jiminy Peak grounds. Corner unit with ample parking, only a short walk to s ...
From $200 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Near Tanglewood: Historic Summer Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly-renovated Berkshire Hills home where rustic charm meets modern elegance. Ideal for families or groups. The open-st ...
From $175 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Berkshires fun at Family Friendly Hygge House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Thank you for checking out Hygge House on Richmond Pond! Hygge (hoo-ga) is the Danish art of enjoying life's simple ple ...
From $500 per night (USD)VRBO
- From $230 per night (USD)
VRBO
SAFE AND COZY BERKSHIRES GETAWAY
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Be one of the first to enjoy this newly-renovated and spotless rental. Our four- season, comfortable home located in th ...
From $230 per night (USD)VRBO
- From $257 per night (USD)
VRBO
Berkshires 4br\/2ba, MEMORIAL TO LABOR DAY, '24
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BERKSHIRES - 4 BR/2BA - Spring &/Or Summer, '24. (Prefer Memorial to Labor Day. PRICE IS BASED ON FULL SEASON RENTAL, BO ...
From $257 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 $430 per night (USD)
VRBO
Richmond Pond Beauty
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
*4.8 Star Winter Wonderland in the heart of the Berkshires. Close to skiing, ice skating, tubing, hiking, etc. Ice fish ...
From $430 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 $638 per night (USD)
VRBO
Modern 4 bedroom lakefront house in The Berkshires.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedroom lakefront house on beautiful Richmond Pond. All new kitchen appliances and bathrooms. Just steps from our bran ...
From $638 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Lovely bright apartment in pastoral shaker barn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Berkshire living at its best! This historic shaker barn on 2 open acres has three apartments. Rent one or more for your ...
From $153 per night (USD)VRBO
- From $277 per night (USD)
VRBO
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Dublinshire Farm is a giant shaker barn that has three private apartments. This newest listing, #3, is a charming 2 sto ...
From $277 per night (USD)VRBO
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Expedia
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 PricingExpedia
- From $384 per night (USD)
VRBO
Berkshires Colonial on 2 Acres by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A Berkshires grand colonial home, on 2.7 private acres is the perfect home-base for your getaway to the Berkshires. Loc ...
From $384 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Charming 2-bedroom cottage with WiFi, AC in lovely Richmond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Escape to tranquility at our charming 2-bed, 1-bath guest cottage in Richmond, MA, nestled in the Berkshires. Perfect fo ...
From $250 per night (USD)Expedia
- From $1300 per night (USD)
VRBO
Stone Villa: 20 minutes to Tanglewood
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
This property is like nothing you've ever seen. After 2 years of renovation, we welcome you to the Stone Manor --a 150-y ...
From $1300 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Caretaker's Cottage: 20 minutes to Tanglewood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 86-acres of forest, streams, wate ...
From $300 per night (USD)VRBO
- From $153 per night (USD)
VRBO
Private apartment in beautiful country barn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Berkshire living at its best! This lovely shaker barn on 2 open acres has three apartments. All are private. Rent one o ...
From $153 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the Berkshires and step back in time with a stay in our charming historic home, conveniently located near the ...
From $125 per night (USD)Expedia
- From $407 per night (USD)
VRBO
Historic New Lebanon Hideaway on 33 Private Acres!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Get the cozy bed and breakfast feel all to yourself at this New Lebanon vacation rental. This sprawling home with 5 beds ...
From $407 per night (USD)VRBO
- From $357 per night (USD)
VRBO
Modern, Renovated Lakefront Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Located in the heart of the Berkshires, and situated on the beautiful Richmond Pond, East Beach Lakehouse is a stylish, ...
From $357 per night (USD)VRBO