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Holiday Rentals and Homes in South Egremont, MA

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    Don't let other travellers get your favourite South Egremont area holiday rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 10 kilometers of South Egremont, Massachusetts.

    1 / 52
    5 of 5 bubbles (10) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 12
    5 of 5 bubbles (5) Excellent
    Alford
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 12
    5 of 5 bubbles (21) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 22
    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Great Barrington, Berkshires 01236
    1 / 10
    5 of 5 bubbles (4) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 bubbles Reviewed 25 July 2016
    Our family of four (two adults and a 12 and 8 year old) recently stayed at Apple Cottage with my sister who lives in Boston and had a wonderful week. The house was perfect for our...
    5 of 5 bubbles Reviewed 16 May 2016
    Tucked away down a country road, farm fresh eggs for breakfast, wonderful rustic cottage details everywhere, Apple Cottage does not disappoint! The cottage easily accommodated 7...
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    1 / 27
    3.5 of 5 bubbles (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Grill
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 bubbles Reviewed 11 September 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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    1 / 14
    5 of 5 bubbles (1) Excellent
    Sheffield
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the... View all property information
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 bubbles Reviewed 28 October 2015
    Beautifully decorated house nestled in the Berkshires. A true getaway. Plenty of room for a family with the latest TV/computer set up. Big kitchen with the best appliances...
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    1 / 14
    5 of 5 bubbles (1) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Satellite TV
    • Patio
    • DVD Player
    • Parking
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Elegant, contemporary one bedroom house sleeps 4. Great central location. Peace, beauty and convenience. Perfectly located for all Berkshires activities, while still maintaining privacy and quiet. All new construction. This is my mother-in-law's property (I handle her online reservations) and... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 19
    5 of 5 bubbles (1) Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 bubbles Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    1 / 10
    4 of 5 bubbles (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 15
    Sheffield
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Washer
    • Waterfront
    • Satellite TV
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Private, 13 Acres, In-Ground Heated Pool, 4 Bdrms, 3&1/2 Baths, Home Office This completely renovated & restored horse barn has been carefully designed, decorated and conceived to guarantee our guests a private & carefree vacation. The main house has 4 bdrms w/ 3&1/2 baths. There is also a... View all property information
    Location Information
    Sheffield, Berkshires 01257
    1 / 18
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Parking
    • Satellite TV
    • Balcony
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berkshire attractions, very private & quiet, abundant wildlife, deer, fox, hawks, turkey.... View all property information
    Location Information
    Great Barrington, Berkshires
    1 / 25
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 6,700 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 13
    Sheffield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • Parking
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors... View all property information
    Location Information
    Sheffield, Berkshires 01257
    1 / 30
    5 of 5 bubbles (3) Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another.... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 15
    Alford
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath... View all property information
    Location Information
    Alford, Berkshires 01266