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Vacation Rentals near Monument Mountain

Route 7, Great Barrington, Massachusetts 01230
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    Travelers to Great Barrington are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    12 Matching Rentals in the Great Barrington AreaView all 18 rentals
    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    Great Barrington
    2.7 miles from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    Great Barrington
    0.9 miles from Monument Mountain
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 34
    (4)Very good
    Great Barrington
    3.8 miles from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Shaker Hill1 / 27
    (2)Average
    Great Barrington
    3.5 miles from Monument Mountain
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,...
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Great Barrington
    2.4 miles from Monument Mountain
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,...
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Great Barrington
    3.8 miles from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful lakeside house is available for vacation rental. MOST SPECTACULAR VIEW OF LAKE BUEL! While most vacation properties only accept a minimum of one week stay, this property offers unique weekend rates for those quick and spontaneous getaways, (August and July excluded, one week stay...
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy and clean in Gt Barrington- available for October1 / 14
    (1)Very good
    Great Barrington
    1.8 miles from Monument Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Private Yard
    • Porch
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking...
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Great Barrington
    2.8 miles from Monument Mountain
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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    The following rentals are within 5 miles of Great Barrington.
    North Egremont
    4.7 miles from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our nearly new home we call RiverSong is on 5.5 acres surrounded by almost 30 more conservation land of meadow and farmland. The pristine Green River is right in our back yard with a wonderful swimming hole. Our Penthouse room is on the upper level of our home. A Bright and spacious king size...
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    Location Information
    North Egremont, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    RiverSong Suite In The Berkshires1 / 52
    (14)Excellent
    North Egremont
    4.7 miles from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Certificate of Excellence
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2018
    We eagerly anticipated our stay at RiverSong. Based on the plethora of five-star reviews we expected near-perfection. While we loved the atmosphere, fabulous comfortable bed...
    Reviewed November 2, 2017
    Riversong suite was wonderful, situated in a great location. Close to nearby restaurants and shops yet far from all the noise. Peaceful and quiet. A great place to renew...
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,...
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    Location Information
    North Egremont, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Smith Farm Homestead1 / 12
    (5)Excellent
    Alford
    4.0 miles from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 4, 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
    Reviewed October 16, 2016
    This is a terrific B&B. Lovely, spacious, comfortable room looking out over rolling pastures and forest. Fabulous breakfasts delivered to your room in a basket: fresh baked...
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    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural...
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    Location Information
    Alford, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    North Egremont
    4.8 miles from Monument Mountain
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book a one-of-a-kind stay in this 5-bedroom, 4.5-bathroom vacation rental home in South Egremont. Built from the bones of a 15th-century British barn, this 4,000-square-foot home for 10 is one of the oldest structures in Massachusetts! Whether you were drawn to the Berkshires by the natural beauty...
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    Location Information
    North Egremont, Berkshires
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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