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

South Egremont Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $541 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite South Egremont area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in South Egremont
    Sort by:
    Default
    The following rentals are within 10 kilometres of South Egremont.
    Berkshires: Romantic Cottage with spectacular view1 / 13
    (21)Excellent
    Popular40 views in the past week
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Apple Cottage1 / 10
    (4)Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    The Smith Farm Homestead1 / 12
    (5)Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Sheffield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • Parking
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (3)Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    Shaker Hill1 / 27
    (2)Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Grill
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    See all reviews
    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    RiverSong Suite In The Berkshires1 / 52
    (10)Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    I was very skeptical about staying somewhere other than a "chain hotel or resort". That is until I met Barbara and Phil. They were a very gracious, humble and warm...
    Reviewed 17 November 2016
    River Song is a wonderfully private and relaxing place to hang your hat before heading out to visit Great Barrington and all the beauty that the Berkshires offers in any season...
    See all reviews
    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>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,...
    View all property information
    Location Information
    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Lake House in the Berkshires1 / 19
    (1)Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    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,...
    View all property information
    Location Information
    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Lakefront Berkshires Ski/Summer House, Great Views1 / 12
    (2)Average
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Ray was very quick to respond to all our rental questions. We had a wonderful weekend at this home. It was very clean and welcoming to our party of 6 . The kitchen was fully...
    See all reviews
    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or...
    View all property information
    Location Information
    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    Sheffield
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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...
    See all reviews
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Internet Access
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the splendor of the Berkshires from this 3-bedroom, 2-bathroom vacation rental house which sleeps 8 in Great Barrington. Situated on a 3-acre lot overlooking the Housatonic River, this home provides an idyllic setting for your retreat. Not only can you relax in the tranquility of your...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Terrace
    • Balcony
    • Housekeeping Included
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded high on a mountainside and surrounded by thousands of acres of state park and conservation land, The Pod is a rustic early 1970's timber and glass octagon set on a concrete pedestal. Decks on four sides with forest or distant mountain views. One stream runs within 15 feet of the master...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Cozy and clean in Gt Barrington- 1 week in summer!1 / 10
    (1)Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    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...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    Alford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2017
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Mountain Views
    • Washer
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    Sheffield
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Mountain Views
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Great Barrington
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • 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...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
    Make Enquiry
    List your property
    Owner log in