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Holiday Rentals near October Mountain State Forest

317 Woodland Rd, Lee, Massachusetts 01238-9219
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    Travellers to Lee are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 30 Rentals in Lee
    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    0.9 miles from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lake House1 / 18
    (4)Excellent
    1.6 miles from October Mountain State Forest
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    The Gatehouse on Golden Hill1 / 13
    (1)Excellent
    1.4 miles from October Mountain State Forest
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    4.7 miles from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • 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!...
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    Lee, Berkshires
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.9 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    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...
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    Lee, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    2.9 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • Balcony
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine....
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    Lee, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    2.9 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed 16 August 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be...
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    Lee, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2.9 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Mountain Views
    • Outdoor Dining Area
    • Balcony
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath...
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    Lee, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2.3 miles from October Mountain State Forest
    1 Bedroom, 2 Bathrooms, Sleeps 10 Quick View
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    • 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...
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 10
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    3.9 miles from October Mountain State Forest
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    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,...
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    Lee, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    2.7 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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...
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4.6 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • Wi-Fi
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    • 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, Marion Father's, nightly entertainment at the Red Lion's Den, close to everything, boutique shops, grocery stores, restaurants, and all Berkshire cultural...
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Berkshire House Share-The Blue Room1 / 10
    (1)Excellent
    1.9 miles from October Mountain State Forest
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Housekeeping Included
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    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....
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    Lee, Berkshires
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 2
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    1.9 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • 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...
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    Lee, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    0.9 miles from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully furnished, 3 bedroom, 2 full bath condo in private, quiet, secluded community, adjacent to October Mt. State Forest. Assigned parking, heated swimming pool, tennis courts and lending library within one block of condo. Open concept living room, dining room and kitchen on first floor. Bedroom...
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    Lee, Berkshires
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gartner House, a charming home in Lenox1 / 21
    (30)Excellent
    2.6 miles from October Mountain State Forest
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 December 2018
    If you are looking to stay in the Berkshire’s and especially in the Lenox area the charming Gartner House, is great option. The location is perfect for exploring Lenox and is...
    Reviewed 20 November 2018
    The perfect place for six girlfriends to catch up. We stayed in Lenox because we all had a day pass at Kripalu for some R&R. The house is so convenient to shopping...
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    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...
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    Lenox, Berkshires
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    4.8 miles from October Mountain State Forest
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
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    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4.9 miles from October Mountain State Forest
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the...
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    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Heart of Lenox1 / 10
    (2)Excellent
    2.7 miles from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 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...
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    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...
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    Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    INTERIOR DESIGNERS BOTANICAL GARDENS1 / 34
    (1)Excellent
    4.9 miles from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Garden
    • Patio
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    We have been traveling to the Berkshires for several years to attend Shakespeare & Company plays. We have stayed at Inns and Hotels. This was our first time, in this area...
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    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING...
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    Lenox, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Heart of the Berkshires!1 / 12
    (2)Very good
    2.7 miles from October Mountain State Forest
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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 29 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...
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    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...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu1 / 24
    (1)Excellent
    4.2 miles from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Mountain Views
    • Balcony
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 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...
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    About this property
    Central Berkshire location! Walk across street to Stockbridge Bowl Beach Lake! Kripalu around the corner, Tanglewood only 1.8 miles to South Gate. Open layout, vaulted ceilings, exposed rafters, ceiling fans, fully equipped kitchen and amenities, washer & dryer. New hypoallergenic Mellanni...
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    Stockbridge, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    4.0 miles from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 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...
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    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...
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    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4.5 miles from October Mountain State Forest
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Hot Tub
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    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...
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    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.7 miles from October Mountain State Forest
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
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    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
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    Stockbridge, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2.8 miles from October Mountain State Forest
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Location Information
    Lenox, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2.7 miles from October Mountain State Forest
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.1 miles from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    19 Century New England classic home renovated to maintain is historical look and feel but with modern kitchen and bathrooms
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    Location Information
    Lee, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.1 miles from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
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    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...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.8 miles from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    2 bed 1 1/2 bath condo fully furnished newly renovated fireplace vaulted ceiling all appliances walk to town Sleeps 6 All new appliances. New furniture March 2017 Near all restaurants, downtown. 1 mile from Tanglewood. Close to Stockbridge Great Barrington, Pittsfield. Many lakes locally...
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    Location Information
    Lenox, Berkshires
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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