Holiday Homes in Stephentown

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Featured Holiday Homes in Stephentown and around

Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (13)
"It's al lovely home. Plenty of room inside and out. Kitchen is well equipped. The wraparound porch is perfect. The pool is very nice. Good location. Tennis courts and a very nice golf course a short drive away. "
Amore Estate - beautiful room with many places to explore and relax in.
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (17)
"The house was recently remodelled and refreshed with contemporary vibe. Thoughtful. Tasteful. Very comfortable to sit and sleep. Artwork is fabulous! Love the screen porch and back patio with grill and firepit. Top of the line grill was clean and easy to use. Kitchen and bathrooms all modern and outfitted perfectly. Everything you need and nothing you don't. Quick walk, bike or drive to Stockbridge center, Tanglewood. Go for a weekend or a week! Just do it."
Stockbridge Home, Come Experience The Berkshires!
Lovely home in historic, residential neighborhood close to RPI
10.0 out of 10, Exceptional, (6)
"Well appointed kitchen and nice little extra welcoming touches from the host. Nice neighborhood. Comfortable back yard. Great wifi. Convenient to grocery and drug stores."
The price is €212
includes taxes & fees
25 Sept - 26 Sept
Lovely home in historic, residential neighborhood close to RPI
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (213)
"We had a great stay at the carriage house! The property was incredible, we especially loved the variety of trails to explore. Our hosts were very helpful with directions and local recommendations. The house was charming and cozy. Would visit again! "
Berkshire Village Carriage House - Super Private!!
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (8)
"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."
Private Access To Laurel Lake, Enjoy Lake Life
Garfield Townhouse in the Berkshires on Main St
10.0 out of 10, Exceptional, (8)
"We very much enjoyed our stay at Garfield House and hope to be back someday. Our host Jeff was responsive and available for anything we needed. The unit was clean and set up just as shown. Highly recommend to anyone interested in staying in a great Berkshire town."
Garfield Townhouse in the Berkshires on Main St
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is €494
includes taxes & fees
9 Sept - 10 Sept
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
10.0 out of 10, Exceptional, (32)
"Relaxing, quiet, beautiful property. We really enjoyed the views, exploring the grounds and it is a short trip to Stockbridge. We had a wonderful stay. "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
10.0 out of 10, Exceptional, (39)
"This was a great location and house; big enough for her entire family. The neighborhood was quiet, the house was clean, all amenities were excellent. The hostess was very communicative and we could not have asked for more. I highly recommend."
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
10.0 out of 10, Exceptional, (2)
"A great place with a lot of charm and space. Beautiful area. Would definitely rent again"
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshire Lake access
10.0 out of 10, Exceptional, (45)
"This is our third year here. We love it Joni is so easy to get a hold of. The house is so clean, it is so nice to not have to bring your own towels, sheets. My kids love the lake and it is quiet which is so nice. There is a fire pit which we usef everyday! Already going to book for next year! "
Berkshire Lake access
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (104)
"We LOVED the house and lake and will definitely be back. Our weekend was very easy and peaceful. The lake is gorgeous and quiet!!! Chris was very helpful with the one or two questions we had. Terrific vacation for us."
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Rockspring by AvantStay | Huge Berkshires Estate
8.6 out of 10, Excellent, (11)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (115)
"Throughly enjoyed the beauty and warmth of the environment. Lots of spaces for us to hang out, cook, and play games. Best of all was the location!!! We were able to hike, kayak and swim at a local beach in addition to all of the cultural pleasures and delicious restaurants and shopping all within a 5 minute drive. It was amazing!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Home away from home
9.0 out of 10, Wonderful, (8)
"Was a beautiful place. Had an issue with the TV but with fast communication host had the problem fixed ASAP. Very quiet and sweet neighbors also. "
Home away from home
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (6)
"The location could not be better in terms of being close to West Stockbridge yet also feeling very remote and with beautiful views. The pool was great. We thoroughly enjoyed ourselves."
Wellspring by AvantStay | Indoor Pool + Views
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (15)
"This was a beautiful, spacious, and peaceful place for us in our friends to get together. It was centrally located to everything we wanted to do. Amanda was wonderful in her communications and everything was clean and ready for us."
The price is €333
includes taxes & fees
11 Sept - 12 Sept
Near Tanglewood: Historic Summer Retreat
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (101)
"This our second time staying here. The house is warm and cozy. . Close to so many activities. Julie is a super host. We had a lovely time. "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
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
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Other property types in Stephentown

Private country home minutes from the Berkshires
5.4 out of 10, (11)
"Do not stay here! I am an international traveler, backpacker, and am used to some rough accommodations, but this stay was truly awful. My friend and I booked the space for a weekend, despite reading the previous reviews, thinking it could not be that bad. The house was overwhelmingly musty, there was mold up into the windowsills, the carpeting felt damp to walk on, and least of all the beds were hard and uncomfortable. We left after one night. It felt like a health hazard to be there. Neither...
The price is €186
includes taxes & fees
9 Sept - 10 Sept
Private country home minutes from the Berkshires
The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1711)
"Excellent amenities with 2 pools, sports courts, an arcade, and great views. "
The price is €176
includes taxes & fees
9 Sept - 10 Sept
Vacation Village in the Berkshires
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.

Recent Reviews in Stephentown
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Stephentown Holiday Homes information

Number of reviews
873
Accommodation
257 Holiday Homes
Lowest Price
€333
Highest Price
€333