20 Best Vacation Rentals in Hancock - Holiday Lettings - Cabins

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109 Vacation rentals

26

Apartment rental in Hancock with shared pool

Berkshires / Hancock

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! Nestled along the scenic border of New York and Massachusetts in the middle of Jiminy Peak Mountain Resort, this pristine Hancock vacation rental …see more

from $185 / night

$1,295 - $2,793 / week

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avg. 44 minutes

from $185 / night

(1) Excellent 

10

Hancock Vacation hotel apartment rental

Berkshires / Hancock

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Lodging at the highest rated resort at Jiminy Peak Mountain--Wyndham Bently Brook Resort-Mountainside What is Jiminy Peak Known For---The Best Skiing in the Berkshire Mountains tucked away in Hancock, Ma. 2 Bedroom Unit consisting of-King bed master, 2 doubles 2nd bedro …see more

from $455 / night

$3,185 / week

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from $455 / night

33

Condo rental in Hancock with indoor pool

Berkshires / Hancock

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Discover an unparalleled vacation destination at Wyndham Bentley Brook. This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal act …see more

from $112 / night

$784 / week

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avg. 2 hours 5 minutes

from $112 / night

(2) Excellent 

16

Cottage rental in Hancock

Berkshires / Hancock

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 201 …see more

from $145 / night

$1,000 / week

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from $145 / night

14

Vacation condo in Hancock

Berkshires / Hancock

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Commanding a stunning view of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pool. Go hiking, biking, fishing or horseback riding around the pr …see more

from $350 / night

$2,450 / week

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from $350 / night

13

Hancock Vacation condo rental

Berkshires / Hancock

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our home on Jiminy Peak! This beautiful, luxury unit 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 accommodates 6+ guests with all the comforts of home. …see more

from $219 / night

$1,533 / week

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Responds fast!
avg. 3 hours 11 minutes

from $219 / night

23

Ski condo to rent in Hancock

Berkshires / Hancock

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly
** Please email or call to confirm availability. Ski-In/Ski-Out Resort! Wyndham Bentley Brook is located right at the base of Jiminy Peak ski mountain, with ski lifts only 200 feet from the resort's front door. In winter, you can ski right out the door to the lifts. I …see more

from $199 / night

$1,400 / week

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from $199 / night

(1) Very Good 

6

Hancock Vacation apartment rental

Berkshires / Hancock

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. …see more

from $250 / night

$1,500 / week

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Responds fast!
avg. 46 minutes

from $250 / night

13

Vacation condo in Hancock

Berkshires / Hancock

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating …see more

from $250 / night

$1,750 / week

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from $250 / night

26

Vacation home in Hancock

Berkshires / Hancock

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Private garden
The vacation house at Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak and to many cultural attractions of the Berkshires, "America's Premier Cultural Resort", including Williamstown Theater Festival, the Clark Art Museum, Hancock Shaker Vi …see more

from $100 / night

$700 / week

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from $100 / night

(3) Very Good 

14

Vacation home with golf nearby in Hancock

Berkshires / Hancock

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly
Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for …see more

from $225 / night

$1,100 / week

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from $225 / night

(1) Excellent 

13

Ski condo to rent in Hancock

Berkshires / Hancock

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly
Steps from the main lifts this 3 Bedroom unit can accommodate up to 8 guests; with all the comforts of home. Master bedroom, with Queen-size bed, wall mounted TV, large closet and a view of the Cricket lift and learning slope. The master bath has duel sinks, jet tub, bo …see more

from $389 / night

$2,723 / week

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Responds fast!
avg. 3 hours 11 minutes

from $389 / night

(1)  

22

Hancock Vacation apartment rental

Berkshires / Hancock

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Bentley Brook Ski-in and Ski-out your front door! 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, …see more

from $167 / night

$1,169 / week

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from $167 / night

(10) Very Good 

21

Ski hotel apartment to rent in Hancock

Berkshires / Hancock

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly
Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northea …see more

from $250 / night

$1,750 / week

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from $250 / night

21

Hancock Vacation apartment rental

Berkshires / Hancock

1 8 3 nights min

  • 1 bedroom
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Bentley Brook Ski-in and Ski-out your front door! 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, …see more

from $144 / night

$1,008 / week

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from $144 / night

(1) Very Good 

4

Vacation home in Hancock

Berkshires / Hancock

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room wit …see more

from $2,500 / night

$29,958 / week

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from $2,500 / night

(2) Very Good 

16

Vacation apartment in Hancock

Berkshires / Hancock

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everyt …see more

from $199 / night

$1,393 / week

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from $199 / night

24

Vacation condo with shared pool in Hancock

Berkshires / Hancock

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
I have this in both 1 and 2Br, so please confirm which you want. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which wee …see more

from $157 / night

$1,099 - $1,999 / week

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Responds fast!
avg. 3 hours 37 minutes

from $157 / night

8

Vacation condo with shared pool in Hancock

Berkshires / Hancock

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
I have qty 2 units available .$1400 each Dec 22 through Dec, 29th-2017 $2650 for both units . Wyndham Bentley Brook / Jimminy Peak Ski Resort ,features indoor and outdoor swimming pools and hot tubs, two fitness centers, sauna, game room, three tennis courts and a picn …see more

from $200 / night

$1,400 / week

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from $200 / night

10

Condo rental in Hancock with shared pool

Berkshires / Hancock

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
Vacation Village in the Berkshires accommodations feature spacious floor plans for maximum comfort. Kitchen, living and dining room in each suite are integrated for entertaining and enjoyment. Designated suites meet Americans with Disabilities Act (ADA) requirements. U …see more

from $158 / night

$1,100 / week

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from $158 / night

24

Vacation condo rental

Berkshires / Hancock

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
Enjoy great year round activities from white water rafting and hiking in the summer, to skiing at the famous Jiminy Peak at this ski in ski out resort. The newly opened Ramblewild Aerial Park is the talk of the town! Your 2 bedroom private condo sleeps 8. It has a ki …see more

from $199 / night

$1,393 / week

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Responds fast!
avg. 3 hours 37 minutes

from $199 / night

20

Studio rental in Hancock with shared pool

Berkshires / Hancock

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Bentley Brook Ski-in and Ski-out your front door! 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, …see more

from $116 / night

$812 / week

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from $116 / night

7

Vacation home rental

Berkshires / Hancock

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
This cozy, converted, modernized barn sits on 171 acres. The wooded location is private and quiet, yet easily accessible. It's a quick drive to all the gems in the Berkshires. Spend a weekend, a week, or more, unwinding. A converted horse barn, "The Barn" has been us …see more

from $150 / night

$1,050 / week

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from $150 / night

88

Vacation home in Hancock

Berkshires / Hancock

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. Suites feature plush bedding, additional sleeper sofa and fully equipped kitchen for all your dining needs. IPOOL, OPOOL, ACTVGUIDE, TENNIS, CEXERCISE, …see more

from $116 / night

$817 / week

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Responds fast!
avg. 2 hours 48 minutes

from $116 / night