Hancock, Massachusetts

Vacation Rentals in Hancock, Massachusetts

Discover 109 vacation rental properties in Hancock. From 1 to 4 bedrooms. Average $354/night. 100% have pools.

109 verified listings Book securely on VRBO Prices updated March 2026

109 properties available

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1 bed 1 bath
PoolA/CWiFiBalcony
$179/night
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In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

1 bed 1 bath
PoolA/CWiFiBalcony
$300/night
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Mountainside Condo Ski In Ski Out

Mountainside Condo Ski In Ski Out

1 bed 1 bath
PoolA/CWiFiBalcony
$149/night
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SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

1 bed 1 bath
PoolA/CWiFiBalcony
$178/night
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Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.

Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
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Mountainside Wyndham Bentley Brook! 2 Bd. dlx.

Mountainside Wyndham Bentley Brook! 2 Bd. dlx.

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
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Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

1 bed 1 bath
PoolA/CWiFiBalcony
$179/night
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Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.

Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
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Ski season is here!

Ski season is here!

2 beds 2 baths
PoolA/CWiFiBalcony
$423/night
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Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

1 bed 1 bath
PoolA/CWiFiBalcony
$179/night
View Details → Book on VRBO
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

1 bed 1 bath
PoolA/CWiFiBalcony
$166/night
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Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
View Details → Book on VRBO
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

1 bed 1 bath
PoolA/CWiFiBalcony
$147/night
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Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

1 bed 1 bath
PoolA/CWiFiBalcony
$178/night
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Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

2 beds 2 baths
PoolA/CWiFiBalcony
$177/night
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Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!

Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!

1 bed 1 bath
PoolA/CWiFiBalcony
$184/night
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Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

1 bed 1 bath
PoolA/CWiFiBalcony
$144/night
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Wyndham Bentley Brook-Ski In/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!

Wyndham Bentley Brook-Ski In/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!

2 beds 2 baths
PoolA/CWiFiBalcony
$164/night
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SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

2 beds 2 baths
PoolA/CWiFiBalcony
$232/night
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Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

2 beds 1 bath
PoolA/CWiFiBalcony
$442/night
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Mountainside Wyndham Bentley Brook! 2 Bd. dlx.

Mountainside Wyndham Bentley Brook! 2 Bd. dlx.

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
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Must See Jurassic Dino Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

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

1 bed 1 bath
PoolA/CWiFiBalcony
$234/night
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Wyndham Bentley Brook! 2 Bd. dlx. in Hancock

Wyndham Bentley Brook! 2 Bd. dlx. in Hancock

2 beds 2 baths
PoolA/CWiFiBalcony
$177/night
View Details → Book on VRBO
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
View Details → Book on VRBO
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

1 bed 1 bath
PoolA/CWiFiBalcony
$173/night
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Outside Adventure-Skiing, Hiking, and Relaxation

Outside Adventure-Skiing, Hiking, and Relaxation

2 beds 2 baths
PoolA/CWiFiBalcony
$169/night
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Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

1 bed 1 bath
PoolA/CWiFiBalcony
$237/night
View Details → Book on VRBO
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

1 bed 1 bath
PoolA/CWiFiBalcony
$310/night
View Details → Book on VRBO
Wyndham Bentley Brook-Ski In/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!

Wyndham Bentley Brook-Ski In/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!

2 beds 2 baths
PoolA/CWiFiBalcony
$168/night
View Details → Book on VRBO
Mountainside Condo @ Jiminy Peak in the Berkshires

Mountainside Condo @ Jiminy Peak in the Berkshires

2 beds 2 baths
PoolA/CWiFiBalcony
$284/night
View Details → Book on VRBO
Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!

Cozy Cabin on resort property in Cultural Berkshires. Pets are welcome!

2 beds 1 bath
PoolA/CWiFiBalcony
$329/night
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SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

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

3 beds 2 baths
PoolA/CWiFiBalcony
$262/night
View Details → Book on VRBO
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

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

1 bed 1 bath
PoolA/CWiFiBalcony
$287/night
View Details → Book on VRBO
Mountainside: Large 3-level Jiminy Peak Home

Mountainside: Large 3-level Jiminy Peak Home

3 beds 3 baths
PoolA/CWiFiBalcony
$434/night
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1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

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

1 bed 1 bath
PoolA/CWiFiBalcony
$248/night
View Details → Book on VRBO
Ski on ski off 1 Br loft condo in the village center with private gated parking

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

1 bed 1 bath
PoolA/CWiFiBalcony
$613/night
View Details → Book on VRBO
Jiminy Peak Mountainside Getaway in the Berkshires

Jiminy Peak Mountainside Getaway in the Berkshires

3 beds 3 baths
PoolA/CWiFiBalcony
$495/night
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Ski In & Ski Out - Deluxe 1 Bedroom Condo

Ski In & Ski Out - Deluxe 1 Bedroom Condo

1 bed 1 bath
PoolA/CWiFiBalcony
$499/night
View Details → Book on VRBO
Beautiful Two Bedroom, Ski In/Out, Mountainside, Home away from Home!

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

2 beds 2 baths
PoolA/CWiFiBalcony
$485/night
View Details → Book on VRBO
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

1 bed 1 bath
PoolA/CWiFiBalcony
$259/night
View Details → Book on VRBO
2 Bedroom Condo, at Jiminy Peak Ski Mountain, Bentley Brook Resort!!

2 Bedroom Condo, at Jiminy Peak Ski Mountain, Bentley Brook Resort!!

2 beds 2 baths
PoolA/CWiFiBalcony
$540/night
View Details → Book on VRBO
Wyndham Bentley Brook-Ski In/Out, Indoor + Outdoor Pools - Only 25% Deposit!

Wyndham Bentley Brook-Ski In/Out, Indoor + Outdoor Pools - Only 25% Deposit!

2 beds 2 baths
PoolA/CWiFiBalcony
$168/night
View Details → Book on VRBO
2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!!

2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!!

2 beds 2 baths
PoolA/CWiFiBalcony
$405/night
View Details → Book on VRBO
Wyndham Bentley Brook Condo Resort

Wyndham Bentley Brook Condo Resort

2 beds 2 baths
PoolA/CWiFiBalcony
$599/night
View Details → Book on VRBO
Wyndham Bentley Brook Condo Resort

Wyndham Bentley Brook Condo Resort

1 bed 1 bath
PoolA/CWiFiBalcony
$483/night
View Details → Book on VRBO
1 Bedroom Deluxe Condo, Sleeps 8, at Bentley Brook, Jiminy Peak Ski Mountain!!

1 Bedroom Deluxe Condo, Sleeps 8, at Bentley Brook, Jiminy Peak Ski Mountain!!

1 bed 1 bath
PoolA/CWiFiBalcony
$445/night
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Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!

Studio Suite, w/ Full Kitchen at Bentley Brook, at Jiminy Peak Ski Mountain!!

1 bed 1 bath
PoolA/CWiFiBalcony
$306/night
View Details → Book on VRBO
Bentley Brook Resort 2 Bedroom

Bentley Brook Resort 2 Bedroom

2 beds 2 baths
PoolA/CWiFiBalcony
$881/night
View Details → Book on VRBO

Showing 48 of 109 properties

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