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Compare 261 Vacation Homes in Stephentown with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 563
SAR 851 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (39)
"The home was convenient to hiking, shopping and dining. It is on a busy street and can be a bit tricky getting in and out of driveway. Inside the home was warm and welcoming. The kitchen had all cooking pans and tools we needed to make meals. There is a great grocery store right down the road. The beds were comfortable and the bathrooms were clean. The hostess was very helpful and attentive when we had a question about the heat. Be aware the staircase to upstairs bedrooms and 2nd bathroom are...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
The price is SAR 432
SAR 1,073 total
includes taxes & fees
12 Jan - 13 Jan
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"This property is close to many Berkshires and Hudson Valley attractions. In addition to its great location, it is clean, has new appliances, and is on such a peaceful street! There is a lot of space, but it's still incredibly cozy. The beds were extra comfy, as well! I will stay here again if the opportunity presents itself. Thanks for a great stay and the easy check-in/check-out process! "
Hudson Valley and The Berkshires getaway

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

9.8 out of 10, Exceptional, (19)
"Such a gorgeous house! We loved walking the nearby trails and how close it was to Williams. Venetia was the best!"
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

3 Bedroom Lakefront Home with Hot Tub & Fireplace

10.0 out of 10, Exceptional, (108)
"Wonderful early Christmas celebration with my adult children! It was beautifully decorated for Christmas including a Christmas tree!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace

Amore Estate - beautiful room with many places to explore and relax in.

9.2 out of 10, Wonderful, (20)
"We had a lovely time on our family holiday trip. Andrea was great- easy to get ahold of, clear communication. The house and neighborhood are so charming. Everything was well stocked, comfortable, and even decorated for the holdiays! We’d love to stay again!"
Amore Estate - beautiful room with many places to explore and relax in.

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views

2 bedroom town house with game room

6.4 out of 10, (13)
"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."
The price is SAR 338
SAR 563 total
includes taxes & fees
11 Jan - 12 Jan
2 bedroom town house with game room

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (18)
"Amanda is a very responsive and accommodating host. The house was comfortable and perfect for our girls weekend with plenty of space for us to relax and feel at home. "
The price is SAR 450
SAR 1,211 total
includes taxes & fees
4 Feb - 5 Feb
Near Tanglewood: Historic Summer Retreat

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (86)
"Simply fantastic!"
Hearts Desire is a furnished whole house in a small, colorful garden center.

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (93)
"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"
A Grand property in Historic Stockbridge

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Stockbridge Home: Walk to Town Beach!

9.8 out of 10, Exceptional, (10)
"A friend and I stayed at this property when the Trauma Healing Immersion event at Kripalu had them fully booked. As someone who normally stays at Kripalu when attended events I was hesitant to find property close enough to create an experience that was still as full of peace and solace as I am used to. This property was just what the dr. ordered. I love the bathroom remodel! It was quiet and peaceful which was just what we needed after a long day of lecture and experiential training. "
Stockbridge Home: Walk to Town Beach!

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (21)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

10.0 out of 10, Exceptional, (18)
"We enjoyed a long weekend at this beautiful home. We had plenty of room for us to spread out. The kitchen is well stocked. They had games in the basement which were an added bonus. The beds were comfortable. We enjoyed relaxing on the porch in the evenings. We would definitely stay here again."
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

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 SAR 1,179
SAR 2,253 total
includes taxes & fees
12 Jan - 13 Jan
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (19)
"Amazing and lovely"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (89)
"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!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
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.
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Other property types in Stephentown

The entire Stephentown Hotel! 28 person occupancy

10.0 out of 10, Exceptional, (1)
"We got 7 families to all stay on the property. Lots of fun. Clean and comfortable sleeping accommodations."
The entire Stephentown Hotel! 28 person occupancy

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1752)
"So enjoyed this property and all the staff was always there to help in anyway!"
The price is SAR 704
SAR 810 total
includes taxes & fees
12 Jan - 13 Jan
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is SAR 709
SAR 778 total
includes taxes & fees
9 Feb - 10 Feb
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.