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Compare Vacation Homes in Stephentown with updated reviews, rates, and availability.

Private Lake House in the Berkshires
Lake Side
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (68)
"What an amazing find to stay at while attending a yoga festival at Jiminy Peak. The house was immaculate and didn't miss a thing! Not only was there a bottle of wine waiting, but an adorable history of the home. The house was HUGE and the beds very comfortable. I wouldn't call it a 3 bedroom house though, it's a 2 bedroom with a pull out sofa in the living room. The hot tub is amazing and watching the starts and fireflies in the backyard at night was magical. Highly recommend and would stay...
Hearts Desire is a furnished whole house in a small, colorful garden center.
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Comfortable New Decor in Living Room Equipped w Smart TV and Deck
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
9.8 out of 10, Exceptional, (59)
"Worked well for our small team. Close enough to the base area to walk."
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
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Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Conveniently located by HVCC. No cleaning or pet fee
Exterior
Conveniently located by HVCC. No cleaning or pet fee
9.6 out of 10, Exceptional, (17)
"We arrived and didnt know what to expect. Everyone proceeded to choose the room that seemed to just fit. We enjoyed the opportunity to sit fireside and plan our days and even had a cook out. Nobody had any complaint about the house. If it were my property i would suggest a no shoes policy. I cant think of any other place i would prefer to stay . It was safe, the neighbors were very nice and our host was the best. Thank you for everything."
Conveniently located by HVCC. No cleaning or pet fee
4 Bdrm Modern Victorian with Tree House and playground
Sophisticated Living Room With Baby Grand Piano
4 Bdrm Modern Victorian with Tree House and playground
9.8 out of 10, Exceptional, (97)
"Great house for our family to stay for my son’s graduation. Galina was wonderful to work with! I highly recommend!"
4 Bdrm Modern Victorian with Tree House and playground
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
A pictureque outdoor dining table on the patio makes al fresco meals a breeze.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, (3)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Fully stocked newly renovated Kitchen.
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (93)
"Everything is basic but solid and comfortable. Beds were nice and firm, my preference. Host was lovely. Wish we could have stayed longer to explore the area more."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
We're ready for Spring & Summer in Upstate NY!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (2)
"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Private Access To Laurel Lake, Enjoy Lake Life
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (6)
"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
Hudson Valley Chalet
Exterior
Hudson Valley Chalet
9.2 out of 10, Wonderful, (5)
"We had such a nice weekend at this beautiful home! The location was great, there were awesome views, and Marc was a very kind, courteous host! He was very easy to get ahold of if we had any questions. The hot tub was very relaxing and spacious. Also, it had all of the necessities. If you are looking for a family-friendly winter rental this is a great place to book."
Hudson Valley Chalet
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Cozy living room nestled between the oversized kitchen and four-season porch.
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
Living area
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
10.0 out of 10, Exceptional, (2)
"This place is where you want to stay if you just want quiet, peaceful, and relaxing times. The host is beyond wonderful and supplied this awesome little tiny house w everything you could ask for and a little bit more. Everything was more than I expected and then some. Very modern amenities and I can’t wait to stay again."
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (206)
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends
Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
9.6 out of 10, Exceptional, (80)
"We loved our stay over Memorial Day weekend. We were three families and fit well in the home with 6 adults, 8 teens and 1 child. Kids loved the pool (it's on the cool side with no heater). The landscaping on the property is so gorgeous. The home itself is very comfortable with many places to spend time together - our favorite is the screened in porch. The two master suites is neat with each having two bedroom spaces per suite. It would be great with a family who wants to have young children...
Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (12)
"we all loved it, especially the screened in porch...& my dog cooper also gives 5 stars"
Stockbridge Home, Come Experience The Berkshires!
Home away from home
Private kitchen
Home away from home
10.0 out of 10, Exceptional, (5)
"nice and quiet location. Close to alot of good food places. Great location for the things we came to do."
Home away from home
Amore Estate - sleeps 12 in beds
October MNT FARM!!
Amore Estate - sleeps 12 in beds
9.6 out of 10, Exceptional, (8)
"Great space for a group of friends! House has a lot of character. Beautiful property and great location! Easy access to downtown Lenox and surrounding area. We really enjoyed our stay!"
Amore Estate - sleeps 12 in beds
2 bedroom town house with game room
Game room
2 bedroom town house with game room
6.0 out of 10, (8)
"Property was easy to get to. Located right off the thruway. House was clean and located close to plenty of shopping options. There was also fast food restaurants located within walking distance. "
The price is AED 312
AED 533 total
includes taxes & fees
22 Jun - 23 Jun
2 bedroom town house with game room
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
9.0 out of 10, Wonderful, (24)
"The cabin was clean and quiet and suited our needs for the weekend. The hot tub was enjoyable, although I would recommend that the owners purchase stairs to make exit and entry a bit easier."
The price is AED 878
AED 1,607 total
includes taxes & fees
28 Jun - 29 Jun
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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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.

Other property types in Stephentown

Private country home minutes from the Berkshires
Property grounds
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 AED 404
AED 738 total
includes taxes & fees
23 Jun - 24 Jun
Private country home minutes from the Berkshires
The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (860)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other noises. I needed a late check out and they were very cool about it. They let me hang out at the pool and then shower at the spa because I was like of stuck there several hours after check out time....
The price is AED 584
AED 641 total
includes taxes & fees
23 Jun - 24 Jun
Jiminy Peak Mountain Resort
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 of Stephentown hotels
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Loved the lake in the back !!!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 2 days ago
The Black Swan Lee - Lenox, Ascend Hotel Collection