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Woodland 5-BR Retreat 5-Min to Jiminy Peak

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Private kitchen
Exterior
Private kitchen
Private kitchen
Dining

Reviews

10 out of 10
Exceptional
5 bedrooms2+ bathroomsSleeps 102162 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Outdoor Space

Explore the area

View in a map
Hancock, MA
  • Place, Jiminy Peak Mountain Resort
    ‪4 min drive‬
  • Place, Taconic Ridge State Forest
    ‪6 min drive‬
  • Place, Mountain Coaster
    ‪6 min drive‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪22 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Double Bed

Bedroom 5

1 Twin Bunk Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet

Spaces

Kitchen
Office
Balcony
Garden

About this property

Woodland 5-BR Retreat 5-Min to Jiminy Peak

Summary:

Nestled in the Berkshires, this 5-BR family home combines comfort and tranquility. The open floor plan connects living areas, and the private backyard has a brand new pool! Bedrooms are spacious, featuring ample natural light. Surrounded by beauty, this home offers a perfect blend of modern living and natural serenity. Home includes a foosball table, and heated pool. Attractions at Jiminy Peak (5-min away), Mt. Greylock (17-min away), and Ramblewild (5-min away).



The Space:

Entire home on Main Street in Hancock.



Guest Access:

Accessible with smart lock.



The Neighborhood:

Located in Hancock. 5-min to skiing at Jiminy Peak!



Getting Around:

Car required.



Other Things to Note:

Notes & Disclaimers:



Wildlife: This is a home in a rural part of the country. You may see wildlife including deer, coyotes, foxes, and bears. Please be mindful of your surroundings and leaving out food and trash. There are Highland cows next door that you may see come to the property line fence. Please do not touch / feed them.



Weather: In the winter, there will be snow, ice, and occasional snowstorms. We recommend driving a vehicle with AWD or 4WD. Please drive with caution and be prepared with regards to the ability of your vehicle to drive in the snow.



Power & Internet: This is a rural part of the country. You may lose power or internet during inclement weather. We do not issue refunds for loss of power or internet out of our control.



Air Conditioning: There's a total of 4 window AC units: in the living-room, dining-room, master bedroom and bunk bedroom. AC availability is seasonal and depending on weather (late spring and summer). Heating is also seasonal, and depending on weather, available during the cold seasons (autumn-winter).



Pool: The pool opens after Memorial Day weekend and closes on October 13th. We recommend contacting us prior to booking to confirm the pool's availability during your stay



Pets: We’re happy to welcome your pup to the home. There’s a $150 fee + tax for the first dog and $50 + tax for each additional one. If you’re planning to bring more than one, please reach out to us before completing your booking so we can get everything set up for you. For everyone’s comfort, we kindly ask that dogs stay leashed outdoors and that you clean up after them. Please note that cats aren’t permitted due to allergy concerns. Any pet-related damages may result in additional charges.



Cancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler’s insurance.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
Charge may apply
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Property Registration Number C0470651210

About the neighborhood

Pittsfield

Located in Pittsfield, this vacation home is in a rural area. The area's natural beauty can be seen at Mount Greylock State Reservation and Mount Greylock State Reservation Visitor Center, while Williamstown Theatre Festival and Hancock Shaker Village are cultural highlights. Mountain Coaster and Alpine Super Slide are also worth visiting.
View more Vacation Homes in PittsfieldOpens in a new window
Map
Hancock, MA

What's nearby

  • Jiminy Peak Mountain Resort - 4 min drive - 4.3 km
  • Taconic Ridge State Forest - 6 min drive - 5.8 km
  • Mountain Coaster - 6 min drive - 5.0 km
  • Zema's Nursery - 7 min drive - 11.5 km
  • Cherry Plain State Park - 10 min drive - 16.8 km

Getting around

  • Pittsfield Intermodal Transportation Center - 25 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 23 min drive

Restaurants

  • ‪Dunkin' - ‬16 min drive
  • ‪Cumberland Farms - ‬4 min drive
  • ‪Old Man Jeff’s Barbecue Company - ‬22 min drive
  • ‪Bob's Country Kitchen - ‬13 min drive
  • ‪Proprietor’s Lodge - ‬20 min drive

Frequently asked questions

Does Woodland 5-BR Retreat 5-Min to Jiminy Peak have a pool?

Yes, this property has a pool.

How much does it cost to stay at Woodland 5-BR Retreat 5-Min to Jiminy Peak?

As of Mar 26, 2026, prices found for a 1-night stay for 2 adults at Woodland 5-BR Retreat 5-Min to Jiminy Peak on May 27, 2026 start from $577, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Woodland 5-BR Retreat 5-Min to Jiminy Peak pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Woodland 5-BR Retreat 5-Min to Jiminy Peak?

Check-in begins at 4:00 PM.

What time is check-out at Woodland 5-BR Retreat 5-Min to Jiminy Peak?

Check-out is at 10:00 AM.

Where is Woodland 5-BR Retreat 5-Min to Jiminy Peak located?

Situated in a rural location, this vacation home is 2.8 mi (4.6 km) from Alpine Super Slide and 3 mi (4.8 km) from Jiminy Peak Mountain Resort. Mountain Coaster and Taconic Ridge State Forest are also within 6 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 14 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.6/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Cathy V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great winter visit to this property. The house was clean, well maintained and felt recently renovated. Located only 5 minutes to Jiminy Peak ski resort, so that was a plus for a house full of skiers. Bedrooms were nice sized and bathrooms were beautiful. One of the nicest VRBO rentals we have found. The only minor complaint was that the outdoor sauna was not functioning during our stay but all agree that we would 100% rent this one again.
Stayed 5 nights in Feb 2026
Verified

10/10 Excellent

Laurel J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Kids thought the best part of their vacation was being at this house!
Stayed 5 nights in Jun 2025
Verified

10/10 Excellent

Haruko F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication and easy check in. The sauna was especially wonderful and relaxing! The house is only minutes away from Jiminy Peak Mountain Resort, where we went to ride the mountain coaster (highly recommend!)
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Erica G.

Liked: Cleanliness, check-in, listing accuracy

Great stay

The house was beautiful, very clean and well kept.
Stayed 2 nights in Jul 2024
Verified

10/10 Excellent

Frank O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property. Seems brand new. The kids got a lot of use of the pool and us adults used the sauna. Our two little puppies had a lot of room to roam. We will consider staying here again in the future
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Rebecca B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to relax and hang out with friends

We booked this house for a weekend getaway to visit friends that live close by. The house is amazing, great island in the kitchen which we would just hang out at. The front porch is great and the pool is 10/10. Bonus of having a solo stove fire pit as well. More than enough room for the 5 adults and 2 kids. Will definitely be booking again!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Amy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful

We stayed here for a Basketball tournament and it was GORGEOUS! Although we did not spend much time in the home it was so comfortable and spacious for our Teammates that did stay with us. I recommended 100% staying here!
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

Barb C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding house

we had rented two houses as there’re were 12 of us and we weren’t up for shared bunks. 'L L
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Christina aka Christine M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family loved the property so much. The main area with the huge kitchen island was the biggest focal point. Everyone commented on the island! The pool was so clean and well maintained and the enclosed fenced in area with the wonderful deck was a hit with our dog and our grandson. The neighborhood was wonderful to walk in. Our family took many walks to the little farm stand. The house was nicely located near Jiminy Peak and Mount Greylock. The huge tv in the family room made for fun movie watching. The house was the perfect size and had such great space for everyone. The hosts were so responsive. We had the best vacation.
We took our family photo sitting in these chairs. They were so comfortable!
The fence was so well built and secured the property so well.
The neighborhood road was quiet and nice place to walk our dog.
Such a great yard. We used the pool and played with our grandson.
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Linda S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy home with great functionality

8 adults. Loved the house. Kitchen perfect in terms of space and supplies. Cozy living area. Beds comfortable. We rent a lot of homes and felt this was one of the best. Will return. Hosts helpful and responsive. Sure will be even better when the pool is completed.
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Michelle S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely loved the house. We took advantage of the sauna and the pool. And we did use the firepit for s’mores one night. It was a perfect house for 7 adults and 4 children. One issue we had was the door locking without us actually turning the lock. We also needed to sweep all the cobwebs off the deck but needed to request a broom. We were also unaware of the mowing company coming to mow the lawn while we were enjoying the pool. And the management company actually sent a message for us to leave the premises before the checkout time even though we were already outside in our cars.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Scott C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house and super clean

This was a great house for six adults to spend most of a week at. It was certainly the cleanest VRBO I've ever rented -- the dishes, silverware and everything in the kitchen was ready to go at check in. Bathrooms and bedrooms were also ultra clean. Kitchen was well stocked with utensils, plates and pots/pans. The rooms were bright both day and night. The large island kitchen was ideal for hanging out at and chatting with friends and family. There is a large yard off to the side of the house, with a pool and fire pit. Also has a nice, heavy duty gas grill. Owners responded quickly to questions. I highly recommend this rental.
Stayed 6 nights in Oct 2024
Verified

10/10 Excellent

Cynthia L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls' Week

We like a house or condo with plenty of bedrooms. The common space was bright with plenty of space for spreading out. I especially appreciated:well-stocked kitchen - more than enough coffee mugs, wine glasses, drinking glasses, plates, etc. We didn't cook much but could have as there were plenty of pots and pans. Appreciated the presence of storage containers, too. plenty of towels - each bedroom was stocked with a double set that included two bath towelsplenty of paper products - tp and paper towels. (would have loved a box of tissues)plenty of cleaning supplies - dish soap, dishwasher soap, laundry detergentplenty of well-marked toiletriesAnd especially, a short checkout list - towels in the bathroom, take out the trash, start the dishwasher, turn out the lights, and lock the door.
Stayed 6 nights in Apr 2025
Verified

10/10 Excellent

Paula M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing fall weekend!

Stayed 2 nights in Sep 2024

About the host

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