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Hancock Vacation Rentals

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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, vacation rental in Hancock
New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, vacation rental in Hancock
New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, vacation rental in Hancock

New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter, vacation rental in Hancock
Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter, vacation rental in Hancock
Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter, vacation rental in Hancock

Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Hancock
Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Hancock
Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Hancock

Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshires Jiminy Peak Mountainside Condo, vacation rental in Hancock
Berkshires Jiminy Peak Mountainside Condo, vacation rental in Hancock
Berkshires Jiminy Peak Mountainside Condo, vacation rental in Hancock

Berkshires Jiminy Peak Mountainside Condo

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Free standing private Ski in/Ski out 4 BR Home on Jiminy Peak, vacation rental in Hancock
Free standing private Ski in/Ski out 4 BR Home on Jiminy Peak, vacation rental in Hancock
Free standing private Ski in/Ski out 4 BR Home on Jiminy Peak, vacation rental in Hancock

Free standing private Ski in/Ski out 4 BR Home on Jiminy Peak

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer, vacation rental in Hancock
Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer, vacation rental in Hancock
Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer, vacation rental in Hancock

Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ski season is coming!, vacation rental in Hancock
Ski season is coming!, vacation rental in Hancock
Ski season is coming!, vacation rental in Hancock

Ski season is coming!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious 3BR 3 BA on Jiminy Mountain 1900 SqFt w Tons of Perks. 5 star property., vacation rental in Hancock
Spacious 3BR 3 BA on Jiminy Mountain 1900 SqFt w Tons of Perks. 5 star property., vacation rental in Hancock
Spacious 3BR 3 BA on Jiminy Mountain 1900 SqFt w Tons of Perks. 5 star property., vacation rental in Hancock

Spacious 3BR 3 BA on Jiminy Mountain 1900 SqFt w Tons of Perks. 5 star property.

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in Hancock
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in Hancock
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, vacation rental in Hancock

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

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Mountainside Condo at Jiminy Peak in the Berkshires, vacation rental in Hancock
Mountainside Condo at Jiminy Peak in the Berkshires, vacation rental in Hancock
Mountainside Condo at Jiminy Peak in the Berkshires, vacation rental in Hancock

Mountainside Condo at Jiminy Peak in the Berkshires

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Home in the Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Hancock
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Hancock
Mountainside: Large 3-level Jiminy Peak Home, vacation rental in Hancock

Mountainside: Large 3-level Jiminy Peak Home

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, vacation rental in Hancock
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, vacation rental in Hancock
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, vacation rental in Hancock

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Unique Yeti-Themed Ski On/Off Suite at Jiminy Mountain - Sleeps 4 -Best Location, vacation rental in Hancock
Unique Yeti-Themed Ski On/Off Suite at Jiminy Mountain - Sleeps 4 -Best Location, vacation rental in Hancock
Unique Yeti-Themed Ski On/Off Suite at Jiminy Mountain - Sleeps 4 -Best Location, vacation rental in Hancock

Unique Yeti-Themed Ski On/Off Suite at Jiminy Mountain - Sleeps 4 -Best Location

Rental Home
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Ski on/off Deluxe Suite on Jiminy Peak Mountain - Sleeps 4 - Best Location, vacation rental in Hancock
Ski on/off Deluxe Suite on Jiminy Peak Mountain - Sleeps 4 - Best Location, vacation rental in Hancock
Ski on/off Deluxe Suite on Jiminy Peak Mountain - Sleeps 4 - Best Location, vacation rental in Hancock

Ski on/off Deluxe Suite on Jiminy Peak Mountain - Sleeps 4 - Best Location

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Cabin on Resort Property with endless fun in Berkshire, vacation rental in Hancock
Cozy Cabin on Resort Property with endless fun in Berkshire, vacation rental in Hancock
Cozy Cabin on Resort Property with endless fun in Berkshire, vacation rental in Hancock

Cozy Cabin on Resort Property with endless fun in Berkshire

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Whitman Woods:  Private Berkshire Vacation, 4 acres, vacation rental in Hancock
Whitman Woods:  Private Berkshire Vacation, 4 acres, vacation rental in Hancock
Whitman Woods:  Private Berkshire Vacation, 4 acres, vacation rental in Hancock

Whitman Woods: Private Berkshire Vacation, 4 acres

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Disney Magic Suite On Jiminy Peak Mtn Resort - Must See Gorgeous - Sleeps 4, vacation rental in Hancock
Disney Magic Suite On Jiminy Peak Mtn Resort - Must See Gorgeous - Sleeps 4, vacation rental in Hancock
Disney Magic Suite On Jiminy Peak Mtn Resort - Must See Gorgeous - Sleeps 4, vacation rental in Hancock

Disney Magic Suite On Jiminy Peak Mtn Resort - Must See Gorgeous - Sleeps 4

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ski On/Off right on Jiminy Peak Mountain . Spacious 2BR sleeps 8.  GORGEOUS!, vacation rental in Hancock
Ski On/Off right on Jiminy Peak Mountain . Spacious 2BR sleeps 8.  GORGEOUS!, vacation rental in Hancock
Ski On/Off right on Jiminy Peak Mountain . Spacious 2BR sleeps 8.  GORGEOUS!, vacation rental in Hancock

Ski On/Off right on Jiminy Peak Mountain . Spacious 2BR sleeps 8. GORGEOUS!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!, vacation rental in Hancock
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!, vacation rental in Hancock
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!, vacation rental in Hancock

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

Rental Home
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Newly renovated, spacious and sunlight filled condo with mountain views, vacation rental in Hancock
Newly renovated, spacious and sunlight filled condo with mountain views, vacation rental in Hancock
Newly renovated, spacious and sunlight filled condo with mountain views, vacation rental in Hancock

Newly renovated, spacious and sunlight filled condo with mountain views

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous Zen Suite- Sleeps 4- Ski On Off Jiminy Mtn- Must See Luxury, vacation rental in Hancock
Gorgeous Zen Suite- Sleeps 4- Ski On Off Jiminy Mtn- Must See Luxury, vacation rental in Hancock
Gorgeous Zen Suite- Sleeps 4- Ski On Off Jiminy Mtn- Must See Luxury, vacation rental in Hancock

Gorgeous Zen Suite- Sleeps 4- Ski On Off Jiminy Mtn- Must See Luxury

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Whitman Woods - A Berkshire Vacation, vacation rental in Hancock
Whitman Woods - A Berkshire Vacation, vacation rental in Hancock
Whitman Woods - A Berkshire Vacation, vacation rental in Hancock

Whitman Woods - A Berkshire Vacation

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Hancock
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Hancock
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, vacation rental in Hancock

Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Year Round Family Mountainside Retreat*Wyndham Bentley Brook - 2 BR Deluxe Suite, vacation rental in Hancock
Year Round Family Mountainside Retreat*Wyndham Bentley Brook - 2 BR Deluxe Suite, vacation rental in Hancock
Year Round Family Mountainside Retreat*Wyndham Bentley Brook - 2 BR Deluxe Suite, vacation rental in Hancock

Year Round Family Mountainside Retreat*Wyndham Bentley Brook - 2 BR Deluxe Suite

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious, Family-Friendly Getaway w/ Full Kitchen & Fireplace, vacation rental in Hancock
Spacious, Family-Friendly Getaway w/ Full Kitchen & Fireplace, vacation rental in Hancock
Spacious, Family-Friendly Getaway w/ Full Kitchen & Fireplace, vacation rental in Hancock

Spacious, Family-Friendly Getaway w/ Full Kitchen & Fireplace

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Family-Friendly Hancock Home: Walk to Slopes!, vacation rental in Hancock
NEW! Family-Friendly Hancock Home: Walk to Slopes!, vacation rental in Hancock
NEW! Family-Friendly Hancock Home: Walk to Slopes!, vacation rental in Hancock

NEW! Family-Friendly Hancock Home: Walk to Slopes!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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1BR Deluxe Suite at Jiminy Mountain Lodge - Sleeps 4 - Best Location, vacation rental in Hancock
1BR Deluxe Suite at Jiminy Mountain Lodge - Sleeps 4 - Best Location, vacation rental in Hancock
1BR Deluxe Suite at Jiminy Mountain Lodge - Sleeps 4 - Best Location, vacation rental in Hancock

1BR Deluxe Suite at Jiminy Mountain Lodge - Sleeps 4 - Best Location

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Bentley/Wyndham Hancock Mass at Jiminy Peak , vacation rental in Hancock
Bentley/Wyndham Hancock Mass at Jiminy Peak , vacation rental in Hancock
Bentley/Wyndham Hancock Mass at Jiminy Peak , vacation rental in Hancock

Bentley/Wyndham Hancock Mass at Jiminy Peak

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Christmas in The Berkshires, vacation rental in Hancock
Christmas in The Berkshires, vacation rental in Hancock
Christmas in The Berkshires, vacation rental in Hancock

Christmas in The Berkshires

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Golden Triangle in the Berkshires, vacation rental in Hancock
Golden Triangle in the Berkshires, vacation rental in Hancock
Golden Triangle in the Berkshires, vacation rental in Hancock

Golden Triangle in the Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, vacation rental in Hancock
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, vacation rental in Hancock
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, vacation rental in Hancock

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vacation Village In The Berkshires 5 Star Resort (Suite B), vacation rental in Hancock
Vacation Village In The Berkshires 5 Star Resort (Suite B), vacation rental in Hancock
Vacation Village In The Berkshires 5 Star Resort (Suite B), vacation rental in Hancock

Vacation Village In The Berkshires 5 Star Resort (Suite B)

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Wyndham Bentley Brook Condo Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, vacation rental in Hancock
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, vacation rental in Hancock
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, vacation rental in Hancock

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in Hancock
Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in Hancock
Wyndham Bentley Brook Jiminy Peak ski in/out unit, vacation rental in Hancock

Wyndham Bentley Brook Jiminy Peak ski in/out unit

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook - Jiminy Peak ski in/out, vacation rental in Hancock
Wyndham Bentley Brook - Jiminy Peak ski in/out, vacation rental in Hancock
Wyndham Bentley Brook - Jiminy Peak ski in/out, vacation rental in Hancock

Wyndham Bentley Brook - Jiminy Peak ski in/out

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Wyndham Bentley Brook at Jiminy Peak ski in ski out, vacation rental in Hancock
Wyndham Bentley Brook at Jiminy Peak ski in ski out, vacation rental in Hancock
Wyndham Bentley Brook at Jiminy Peak ski in ski out, vacation rental in Hancock

Wyndham Bentley Brook at Jiminy Peak ski in ski out

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Jiminy Peak ski in/ski out Wyndham Bentley Brook, vacation rental in Hancock
Jiminy Peak ski in/ski out Wyndham Bentley Brook, vacation rental in Hancock
Jiminy Peak ski in/ski out Wyndham Bentley Brook, vacation rental in Hancock

Jiminy Peak ski in/ski out Wyndham Bentley Brook

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Wyndham Bentley Brook at ski in/ ski out Jiminy Peak, vacation rental in Hancock
Wyndham Bentley Brook at ski in/ ski out Jiminy Peak, vacation rental in Hancock
Wyndham Bentley Brook at ski in/ ski out Jiminy Peak, vacation rental in Hancock

Wyndham Bentley Brook at ski in/ ski out Jiminy Peak

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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IN/OUT SKIING  CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES, vacation rental in Hancock
IN/OUT SKIING  CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES, vacation rental in Hancock
IN/OUT SKIING  CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES, vacation rental in Hancock

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

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in Hancock
Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in Hancock
Bentley Brook ski in/ski out at Jiminy Peak, vacation rental in Hancock

Bentley Brook ski in/ski out at Jiminy Peak

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool, vacation rental in Hancock
Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool, vacation rental in Hancock
Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool, vacation rental in Hancock

Get Away to the Berkshires: 1 Bedroom Luxury Condo with Outdoor Pool

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Bentley Brook Jiminy Peak ski in ski out, vacation rental in Hancock
Bentley Brook Jiminy Peak ski in ski out, vacation rental in Hancock
Bentley Brook Jiminy Peak ski in ski out, vacation rental in Hancock

Bentley Brook Jiminy Peak ski in ski out

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Accommodations w/ Fireplace, Full Kitchen & More!, vacation rental in Hancock
Cozy Accommodations w/ Fireplace, Full Kitchen & More!, vacation rental in Hancock
Cozy Accommodations w/ Fireplace, Full Kitchen & More!, vacation rental in Hancock

Cozy Accommodations w/ Fireplace, Full Kitchen & More!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Full Week of Ski-in,Ski-out * Jiminy Peak Club Whyndam Bently Brook in Berkshire, vacation rental in Hancock
Full Week of Ski-in,Ski-out * Jiminy Peak Club Whyndam Bently Brook in Berkshire, vacation rental in Hancock
Full Week of Ski-in,Ski-out * Jiminy Peak Club Whyndam Bently Brook in Berkshire, vacation rental in Hancock

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

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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UMIQUE Country Condo, 1BR 1 BA - NEW, vacation rental in Hancock
UMIQUE Country Condo, 1BR 1 BA - NEW, vacation rental in Hancock
UMIQUE Country Condo, 1BR 1 BA - NEW, vacation rental in Hancock

UMIQUE Country Condo, 1BR 1 BA - NEW

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in Hancock
Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in Hancock
Jiminy Peak Mountainside Getaway in the Berkshires, vacation rental in Hancock

Jiminy Peak Mountainside Getaway in the Berkshires

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ski-in/Ski-out - Club Wyndham Bentley Brook - Jiminy Peak, vacation rental in Hancock
Ski-in/Ski-out - Club Wyndham Bentley Brook - Jiminy Peak, vacation rental in Hancock
Ski-in/Ski-out - Club Wyndham Bentley Brook - Jiminy Peak, vacation rental in Hancock

Ski-in/Ski-out - Club Wyndham Bentley Brook - Jiminy Peak

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Hancock
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Hancock
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook, vacation rental in Hancock

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Hancock