We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes near October Mountain State Forest

256 Woodland Rd., Lee, Lee, Massachusetts
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $377 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Lee are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 25 Rentals in Lee
    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    4.4 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4.3 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    chestnut lodge Queens Room1 / 2
    (1)Excellent
    4.4 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4.6 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Shared Garden
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the second floor of the barn. this is very rustic, literally a barn! Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot...
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    4.4 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you...
    View all property information
    Location Information
    Lee, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 6
    Make Enquiry
    The Gatehouse on Golden Hill1 / 13
    (1)Excellent
    2.6 kilometres from October Mountain State Forest
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2017
    Stayed for 4 nights. Very spacious and well maintained. Greeted by Peter with prosecco, cheese, crackers,tomatoes, mint from the garden, and donuts. He gave us an orientation...
    See all reviews
    About this property
    We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the 'Gatehouse' to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring,...
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Enquiry
    7.7 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!...
    View all property information
    Location Information
    Lee, Berkshires
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Lake House1 / 18
    (4)Excellent
    3.0 kilometres from October Mountain State Forest
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2016
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences...
    Reviewed 2 September 2016
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
    See all reviews
    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located...
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
    Make Enquiry
    5.9 kilometres from October Mountain State Forest
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,...
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    7.7 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Grill
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All New, renovated 400 sq. ft. cottage is located centrally in South Lee, / Stockbridge line. Only 1 mile from Stockbridge main street, nightly entertainment at the Red Lion's Den, close to everything, boutique shops, grocery stores, restaurants, and all Berkshire cultural attractions. Live...
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Save time - get the best Lee rentals sent straight to your email!
    Get the List
    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    1.6 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on...
    See all reviews
    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock...
    View all property information
    Location Information
    Lee, Berkshires
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Berkshire House Share-The Blue Room1 / 10
    (1)Excellent
    3.3 kilometres from October Mountain State Forest
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated home in the Berkshire Mountains of Western MA. I would prefer a long-term housemate, but will be glad to do weekend or short term stays. Long-term pricing can be negotiable. Cable TV (in your room), internet, washer and dryer, big eat-in kitchen, well-lit living room....
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 2
    Make Enquiry
    7.2 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1400 square foot, three bedroom home has all amenities including washer and dryer in basement. Electric heat and oven. Front porch and back deck. First floor is open floor plan with kitchen, dining area and living room flowing from one to the other. Skylights in the living/dining area and...
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3.3 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Central Heating
    • Porch
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a...
    View all property information
    Location Information
    Lee, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
    Make Enquiry
    3.8 kilometres from October Mountain State Forest
    1 Bedroom, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Washer
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that homeowner lives in a separate building on the property and may be present during your stay* Gather your loved ones for a revitalizing Lee retreat when you book this lovely 3-bedroom, 2-bathroom vacation rental house that comfortably sleeps 10! With new furnishings, a private...
    View all property information
    Location Information
    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Gartner House, a charming home in Lenox1 / 21
    (28)Excellent
    4.7 kilometres from October Mountain State Forest
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2018
    We had a wonderful time staying at this property as a family. It’s spacious and beautifully designed. It’s elegant cozy.
    Reviewed 11 January 2018
    This place is everything that is promised in the description. We have rented a place before that was better equipped with amenities. Proximity to Lennox, Pittsfield, Stockbridge...
    See all reviews
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore...
    View all property information
    Location Information
    Lenox, Berkshires
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)1 / 17
    (1)Excellent
    7.3 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Mountain Views
    • Balcony
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2018
    Great location, 2 minute walk to the beach with a view of the mountains and a very short drive to Tanglewood, Norman Rockwell Museum and all local attractions.Cindy and Paul are...
    See all reviews
    About this property
    The Stockbridge Bowl Lake Beach cottage is centrally located in Berkshire County in Stockbridge, MA. Walk across the street to Stockbridge Bowl Town Beach. We provide the beach chairs and towels. Lovely furnishings, fully equipped kitchen with new small appliances and amenities. Open cottage feel...
    View all property information
    Location Information
    Stockbridge, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Heart of Lenox1 / 10
    (2)Excellent
    4.9 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    1/2 house, with owners in other half, which was handy for questions and suggestions. Very clean, and queen bed was really comfortable. Other BR has twin bedsKitchen has...
    Reviewed 28 May 2017
    Title sums it up! Excellent choice for our recent visit to Lenox. The house is very clean and comfortable and the owners are very accommodating. Location is great, just steps...
    See all reviews
    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
    View all property information
    Location Information
    Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Heart of the Berkshires!1 / 12
    (2)Very good
    4.8 kilometres from October Mountain State Forest
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    A friend and I rented this charming home for 3 nights. It was immaculate, the kitchen was well stocked, furniture/beds comfortable. The bedrooms had window a/c units. What...
    Reviewed 30 June 2017
    I was looking for a place for two couples for a weekend in the Berkshires, and stayed at this house. It was a perfect fit for my needs. The house is on a road that has very...
    See all reviews
    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest...
    View all property information
    Location Information
    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Family-friendly Cottage Near Lake, Tanglewood1 / 32
    (6)Excellent
    7.0 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    Location was fantastic. Sarah (the owner) provided some great advice on local farmers markets and hikes. The beach was a quick walk from the cottage where we could paddle on...
    Reviewed 31 July 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
    See all reviews
    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd...
    View all property information
    Location Information
    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    7.6 kilometres from October Mountain State Forest
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master...
    View all property information
    Location Information
    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    5.0 kilometres from October Mountain State Forest
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road...
    View all property information
    Location Information
    Lenox, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    3.6 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    19 Century New England classic home renovated to maintain is historical look and feel but with modern kitchen and bathrooms
    View all property information
    Location Information
    Lee, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4.9 kilometres from October Mountain State Forest
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No matter the season, you'll find the getaway you crave while staying at this 3-bed, 2.5-bath house in Lenox! This welcoming vacation rental features room for 6, numerous amenities, and an incredible location just minutes from the Tanglewood Music Center. In addition, enjoy easy access to the...
    View all property information
    Location Information
    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    7.1 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy leisurely lakeside days just a walk away as you stay at this 3-bed, 1.5-bath vacation rental house that sleeps 6 in Stockbridge! With mossy grounds below and age-old oaks towering above, this cozy cottage is a dreamy retreat, perfect for those looking for a bit of the great outdoors without...
    View all property information
    Location Information
    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in