Photo by Leah Dalley

Holiday Homes in South Egremont

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Featured Holiday Homes in South Egremont

Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is AU$740
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (20)
"Lovely home, dog friendly ! Amazing stay, great location. "
Stockbridge Home, Come Experience The Berkshires!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is AU$488
includes taxes & fees
29 Sept - 30 Sept
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Relax or be active! The choice is yours in this pet-friendly family home.
10.0 out of 10, Exceptional, (6)
"The house was so New England! Huge yard private setting. House was fully stocked and the kitchen had great appliances with anything you would need . Deck off the kitchen was so nice . Plenty of space to spread out . I would definitely recommend this home to anyone ! Thanks Terri Marino"
Relax or be active! The choice is yours in this pet-friendly family home.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (34)
"My grown daughter and I stayed here for a two night visit to the Berkshires. It was so nice to have an entire house rather than a hotel room! We received our check in email in plenty of time, the house was clean and furnished with generous amenities such as soaps, shampoos, coffee, etc., the owner was readily available. The house is close to the road, but it really wasn’t a problem…white noise machines and air purifiers made sleeping very comfortable, and there was very little traffic noise....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (64)
"Perfectly located and lovely appointments make this the place to stay when visiting Lenox, Tanglewood, etc. The home is farm in style but elegantly decorated with thoughtful combinations of old and new. Well laid out floor plan allows groups to host friends and families at the same time. You will be delighted by mornings in the kitchen or evenings in the living spaces. Enjoy! "
Enjoy comfortable elegance in this secluded grand home located in town
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (17)
"At the end of a dead-end street but only two blocks from the center of Stockbridge, this century-old charmer may be the best-kept and best-supplied rental in the Berkshires. We stayed a month(!) and loved it. The location is unbeatable, an easy walk from the Red Lion and within 15 minutes of Tanglewood, The Mount, the Rockwell museum and other attractions. Four local trails begin 100 feet away, including the Ice Glen. A beautiful, productive garden awaits, and the screened front porch may be...
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (38)
"We had a lovely weekend at Alex's home. We had everything we needed as the house was well stocked. Alex was very quick to respond to all our inquiries! We loved the central location and the fireplace was perfect for the cool nights! We hiked, shopped and enjoyed the board games at night! Would recommend! "
Cozy Retreat on Copake Lake in our Charming Home
Whitney by AvantStay | Private Berkshires Estate
8.0 out of 10, Very good, (7)
"We spent a lovely 2 weeks here. We had some septic issues that were remedied quickly. Overall, the house was comfortable and provided easy access to all the Berkshires have to offer."
Whitney by AvantStay | Private Berkshires Estate
Your Invited to the Berkshires!
9.8 out of 10, Exceptional, (29)
"Clean, updated home in the perfect location. Loved the screens in porch! Holly is a wonderful host and her home is a perfect getaway."
Your Invited to the Berkshires!
Mountain View Getaway
10.0 out of 10, Exceptional, (41)
"This is our second year staying with at Karen and Larry’s property and it did not disappoint. They are incredible hosts and their home is conveniently located near the Lime Rock Track (less than 3 miles). It’s a beautiful and peaceful setting and extremely comfortable home. We highly recommend."
Mountain View Getaway
Peace and quiet on the lake
9.6 out of 10, Exceptional, (190)
"Loved it!"
Peace and quiet on the lake
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (40)
"I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Fox Hollow Luxury Ranch Laurel Lake
8.8 out of 10, Excellent, (16)
"Very quiet central location in the Berkshires. Close to all amenities. Enjoyed the lake canoeing and site seeing. Great house with everything needed. "
Fox Hollow Luxury Ranch Laurel Lake
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (24)
"We stayed at the Meadow House over Labor Day weekend. Lars was super accommodating to us and made sure we were taken care of. Really quick responses from him and he’s even working with us to return something one of the friends I was with left behind. Definitely recommend this house if you’re looking to escape the city or go hiking near by."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
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Other property types in South Egremont

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (83)
"The owner was fantastic! Super kind and accommodating. Very available for any help or questions. Well maintained, clean and quiet property. Would definitely stay there again! "
The price is AU$177
includes taxes & fees
11 Oct - 12 Oct
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (36)
"Communication with property manager was seamless, and above any previous interactions I have ever had. Great place. Well maintained. Clean. Stocked with basic kitchenware and cleaning material. Great Wifi. Tennis Court was such a nice bonus. Would 100% (and will likely) stay here again!"
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.