Pittsfield State Forest Vacation Rentals

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Vacation Rentals in Pittsfield State Forest

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2126)
"Clean and great pool and hot tub facilities "
United States
Alyce
$112 nightly
The price is $125
Nov 12 - Nov 13
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
$149 nightly
The price is $166
Nov 10 - Nov 11
Total with taxes and fees
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
$125 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
$165 nightly
The price is $183
Nov 10 - Nov 11
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$253 nightly
The price is $283
Nov 10 - Nov 11
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
$262 nightly
The price is $291
Nov 10 - Nov 11
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$666 nightly
The price is $743
Nov 16 - Nov 17
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
$1,026 nightly
The price is $1,111
Nov 18 - Nov 19
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Outdoor banquet area
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham
9.6 out of 10, Exceptional, (93)
"The house was very clean and well stocked. There were so many fun things to do - swimming pool, ping pong, darts, air hockey, gym, pinball, basketball hoop, foosball, etc. it was a great house for 4 families. The owner was very communicative and responded quickly to questions about the neighborhood, it was also very well located. Highly recommend!"
United States
Daisy H.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (132)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
8.8 out of 10, Excellent, (6)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
$533 nightly
The price is $540
Nov 10 - Nov 11
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Property grounds
The Lakeshore House

The Lakeshore House

Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
$716 nightly
The price is $802
Nov 10 - Nov 11
Total with taxes and fees
The Lakeshore House
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Smart TV, fireplace, DVD player, music library
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Pownal
9.4 out of 10, Exceptional, (84)
"Great communication from the hosts and convenient to Williamstown, Bennington and all things VT. Clean and comfortable. Look forward to coming back!"
United States
Emily N.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience

Sand Lake
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
$165 nightly
The price is $183
Nov 11 - Nov 12
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lee
9.4 out of 10, Exceptional, (70)
"Liked the 3 room suite, and 100 year old oak interior and the front porch, esp. as time went on. Walk to many restaurants, some only open in Fall after Wednesday. Some of the old doors fit like old doors, not unexpected, and felt like home away from home as time went on. Liked Fridge, coffee maker and small kitchen that we hardly used, but would have used more if longer stay."
United States
Leonard
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield State Forest Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Excellent staff and room. "
Philip 2-night trip
Posted 16 hours ago
Hotel On North

Find out more about Pittsfield State Forest

Everything you need to know about Pittsfield State Forest vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield State Forest vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield State Forest vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsfield State Forest vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield State Forest. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pittsfield State Forest in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsfield State Forest rentals

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To find some top Pittsfield State Forest rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield State Forest vacation.

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