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Apartment Rentals and Condos in Pittsfield, MA and nearby

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    1 / 20
    5 of 5 stars (2) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 8
    4 of 5 stars (2) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Pittsfield
    7 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    1 / 47
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Balcony
    • DVD Player
    • Terrace
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to our home! This beautiful, luxury unit is fully equipped with everything a family will need for the perfect Mountainside vacation. 3 Bedrooms accommodates 8 guests with all the comforts of home. Master bedroom, with Queen-size bed, wall mounted TV, large closet and a view of the... View all property information
    Location Information
    Pittsfield, Berkshires

    The following rentals are within 10 miles of Pittsfield, Massachusetts.

    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
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    • x
    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed June 17, 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Outdoor Dining Area
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed June 17, 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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    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Sauna
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed February 18, 2016
    My family and I come here every February to snowboard/ski. My boys are in their 20's and they still want to come here with the family and have fun. This year though my husband...
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Internet Access
    • Porch
    • Parking
    • Mountain Views
    • Satellite TV
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 2 nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
    Location Information
    Lee, Berkshires 01238
    Lee
    Private Room, 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
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Lee, Berkshires 01238
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Washer
    • Mountain Views
    • Patio
    • Grill
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! This excellent property carries an abundance of amenities to make your northeast vacation one you’ll always cherish. Nestled along the scenic border of New York and... View all property information
    Location Information
    Hancock, Berkshires 01237
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    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
    • Private Yard
    • Patio
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Lenox, Berkshires 01240
    Lee
    1 Bedroom, 3 Bathrooms, Sleeps 5 | Quick View
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    • Grill
    • Patio
    • Shared Yard
    • Parking
    • Mountain Views
    • Wi-Fi
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    This is the second floor of the 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 pot and coffeemaker. Bathroom has... View all property information
    Location Information
    Lee, Berkshires 01238
    1 / 10
    5 of 5 stars (14) Excellent
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Internet Access
    • DVD Player
    • Shared Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. We are about 8 minutes away from Jiminy Peak and... View all property information
    Location Information
    Lanesboro, Berkshires 01237
    5 of 5 stars Reviewed February 12, 2016
    My boyfriend and I celebrated my birthday weekend at the cottage. We had a rough start the day we were to arrive and Cheryl was just wonderful and so understanding. We were...
    5 of 5 stars Reviewed October 5, 2015
    My husband and I just returned from a fabulous weekend getaway in the Berkshires. We chose the Stone School Cottage but it's privacy, central location, and unique character. We...
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    1 / 21
    5 of 5 stars (21) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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 01240
    5 of 5 stars Reviewed January 20, 2016
    My friends and I loved the Gartner home. It was conveniently located to downtown Lenox, cozily furnished and spotlessly clean. The eat in kitchen was well stocked with everything...
    4 of 5 stars Reviewed October 16, 2015
    We were here during the 2015 foliage season. Absolutely beautiful. The house was very roomy and very comfortable. Has all the amenities you need in kitchen and other rooms...
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
    Location Information
    Lenox, Berkshires 01240
    1 / 10
    4.5 of 5 stars (6) Very good
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
    Location Information
    Richmond, Berkshires 01254
    3 of 5 stars Reviewed October 26, 2015
    Better directions to the house would have been helpful. For two nights my daughter and two granddaughters joined us and found the yard and swingset fun. The weather was quite...
    5 of 5 stars Reviewed September 7, 2015
    This house was very comfortable and quiet. We had everything that we needed in the house. The house was clean. The beds were comfortable and cozy. The neighborhood was also quiet...
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    1 / 46
    5 of 5 stars (1) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 25 | Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed May 29, 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 with full wet bar & flat screen... View all property information
    Location Information
    Hancock, Berkshires 01237
    4 of 5 stars Reviewed August 11, 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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    Cheshire
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study,... View all property information
    Location Information
    Cheshire, Berkshires 01225
    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed August 16, 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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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Parking
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    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden.... View all property information
    Location Information
    Lenox, Berkshires 01240
    1 / 16
    4.5 of 5 stars (2) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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. Everything you need on your... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed September 5, 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    4 of 5 stars Reviewed October 25, 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Private Indoor Pool
    • Sauna
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 activities, return to your... View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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, 2014 - Seot 2, 2014 $7500 Summer... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed July 30, 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    1 / 24
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Parking
    • DVD Player
    • Satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Porch
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
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    Lee, Berkshires 01238
    1 / 12
    4 of 5 stars (1) Very good
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Grill
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    • Central Heating
    • Porch
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
    Location Information
    Lenox, Berkshires 01240
    4 of 5 stars Reviewed July 8, 2015
    Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the...
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    1 / 15
    Lenox Dale
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    About this property
    Ref # 369305 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. We believe elevating where you live is about blending it seamlessly with how you live.... View all property information
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    Lenox Dale, Massachusetts
    1 / 17
    5 of 5 stars (2) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
    • Grill
    • Internet Access
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    • Mountain Views
    • Hot Tub
    • Outdoor Dining Area
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed October 11, 2015
    Rustic and vintage are apt descriptions of the house itself. It has stories to tell! And to matched its abundant, well aged charm is the friendly and generous host. Joanne made us...
    5 of 5 stars Reviewed June 12, 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    1 / 24
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Booking now for Fall 2016; the summer season is sold out, except for the last week in August! Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic... View all property information
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    Lee, Berkshires 01260
    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Patio
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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    Richmond, Berkshires 01254
    1 / 19
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham 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, enjoy hiking and horseback... View all property information
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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed September 9, 2015
    The units are clean and spacious and well stocked. Movie theater, swimming pools, outdoor picnic area with grills. and the mountain adjacent has plenty of outdoor activities...
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    1 / 19
    5 of 5 stars (2) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
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    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 01238
    5 of 5 stars Reviewed October 29, 2015
    The Lake House was paradise. It is situated right in The Berkshires on Rte. 20 with easy access to everything. We golfed, canoed, played tennis, swam, hiked, went to museums...
    5 of 5 stars Reviewed October 27, 2015
    We were a group of 8 friends who have vacationed together annually. This was by far the best appointed house we have rented in 30 years. The owners, Margie and Frank were...
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    1 / 5
    Lenox Dale
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Ref # 370996 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Located on the second Chinatown Quincy , 6-minute walk to the Red Line subway station... View all property information
    Location Information
    Lenox Dale, Massachusetts
    Lenox
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
    • Mountain Views
    • Hot Tub
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    • Shared Indoor Pool
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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    Lenox, Berkshires 01240
    1 / 15
    Lenox Dale
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
    • ?
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    Ref # 369307 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. We believe elevating where you live is about blending it seamlessly with how you live.... View all property information
    Location Information
    Lenox Dale, Massachusetts
    Lenox
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the... View all property information
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    Lenox, Berkshires 01240
    1 / 27
    Lenox Dale
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Ref # 364815 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. This property is what most travelers wish to find and rarely do. This apartment is... View all property information
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    Lenox Dale, Massachusetts
    1 / 15
    Lenox Dale
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    Ref # 369306 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. We believe elevating where you live is about blending it seamlessly with how you live.... View all property information
    Location Information
    Lenox Dale, Massachusetts
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    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
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    Lee, Berkshires 01238
    1 / 23
    Lenox Dale
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • ?
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    Ref # 364820 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. AMENITIES Easy Walk to the Subway Convenient Off-street Parking for 2 cars with... View all property information
    Location Information
    Lenox Dale, Massachusetts
    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Located in the tranquil hills of the beautiful Berkshires. This truly is a wooded wonderland filled with restful beauty and abundant wildlife. Wonderful retreat in the Berkshires. Private and secluded. Minutes from Tanglewood, The Red Lion Inn and The Norman Rockwell museum. Skiing. Private lake... View all property information
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    Lee, Berkshires 01238
    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Mountain Views
    • Grill
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    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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 everyone yet a very cozy... View all property information
    Location Information
    Hancock, Berkshires 001237
    Lanesboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and all the furnishings are new... View all property information
    Location Information
    Lanesboro, Berkshires 01224
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak (less than 5 minutes away) and to many cultural attractions of the Berkshires including Williamstown Theater Festival and Tanglewood. For outdoor lovers, Whitman Woods is near Mount Greylock Reservation, Audubon's... View all property information
    Location Information
    Hancock, Berkshires 01237
    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
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    Lee, Berkshires 01238
    1 / 25
    5 of 5 stars (9) Excellent
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed June 22, 2016
    This was a perfect weekend retreat for our extended family of six (three adult couples). The house is very warm and inviting, clean, and well-equipped. The surrounding woods and...
    5 of 5 stars Reviewed July 7, 2015
    My eight year old daughter and I had a wonderful time staying in Hancock. We were joined at different times by young cousins and grandparents - the kids loved the inside (the bunk...
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    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Outdoor Dining Area
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    • Shared Yard
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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    Hinsdale, Berkshires 01235
    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Skiing: Property Is...
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    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 Northeast! Wyndham Bentley Brook... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed March 23, 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    4 of 5 stars Reviewed January 26, 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
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    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Mountain Views
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 and fitness room. Indoor... View all property information
    Location Information
    Hancock, Berkshires 01237
    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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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,... View all property information
    Location Information
    Lee, Berkshires 01238