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Compare 268 Vacation Homes in Stephentown with updated reviews, rates, and availability.

"Property was very nice Kirchen could use some additons -starting with a ladle "

AED 841 total

includes taxes & fees

25 Feb - 26 Feb

"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"

AED 2,472 total

includes taxes & fees

24 Feb - 25 Feb

Gorgeous chef with 6 burner professional gas range

"Great house"

Comfortable New Decor in Living Room Equipped w Smart TV and Deck

"Location was very Close to trail"

AED 2,229 total

includes taxes & fees

24 Feb - 25 Feb

It may be cold outside, but it's warm & cozy inside!

"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"

"We thoroughly enjoyed our stay at “Hearts Desire”! Everything was set up for our relaxation and enjoyment! The weather outside was terrible but the atmosphere in the house was warms and so comfortable. We were able to enjoy watching the tv which sometimes doesn’t give many choices in some other stays. We are definitely getting the game “Fake News or Not”! Lots of fun. If we plan on visiting the area again, we will definitely return! Thank you!"

"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...

"As advertised "

"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "

AED 1,093 total

includes taxes & fees

24 Feb - 25 Feb

"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"

AED 3,898 total

includes taxes & fees

25 Feb - 26 Feb

"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "

"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "

Breakfast Nook - wake up to the best sunshine ever!

"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "

"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"

AED 1,192 total

includes taxes & fees

27 Feb - 28 Feb

Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access

"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....

"Comfortable and presentable. Location is great for going downtown or shopping in general. Restaurants are very close by. Property manager was easy to communicate with."

AED 650 total

includes taxes & fees

22 Mar - 23 Mar

Second story deck with lake views, dining table for 8, sitting area and grill

"This was our third year in a row staying at this house for our annual ski trip with 4 adults and 6 kids. It is always immaculate and has great common rooms for all of us. Kari and Glenn think of everything and Glenn even came to shovel the walkway and driveway for us during a snow storm (without even having to enter the house). We look forward to our time at this beautiful property every year! "

"We had an amazing time. We had several out of town guests who stayed at the home and then a birthday party with local guests in the ballroom. The ballroom is absolutely stunning. The chef enjoyed the kitchen. There was plenty of parking and a beautiful setting. I would stay again. "

"Chip and Kim are exceptional hosts, and we enjoy coming to this property every Thanksgiving to gather as a family. It meets all of our needs, and we love it!"