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Compare 60 Cottages in Stephentown with updated reviews, rates, and availability.

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (13)
"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"
Cozy cottage with pool, walking distance to lake

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (23)
"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"
Cozy Berkshire cottage with fireplace.

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (105)
"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."
Charming historic cottage on scenic road to Mt. Greylock

15 Minutes From Jiminy Peak/Secluded Lake Lodge on Crooked Lake

10.0 out of 10, Exceptional, (8)
"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."
15 Minutes From Jiminy Peak/Secluded Lake Lodge on Crooked Lake

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Cottage in the Clouds With Mountain Views

9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "
Picturesque Cottage with Sunroom on Ashmere Lake!

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!

Chic Troy Home Near Downtown, 9 Mi to Albany!

3.0 star property
8.0 out of 10, Very Good, (1)
Chic Troy Home Near Downtown, 9 Mi to Albany!

Eclectic Troy Home w/ Hot Tub - Pet Friendly!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This place is awesome. We weren't there much as it was parents weekend for RPI but it was so great to come back to a house with a hot tub and sauna. I thought we would use the pool table but the weekend ended up too busy to invite friends over. Super comfortable and beautiful."
Eclectic Troy Home w/ Hot Tub - Pet Friendly!

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3.0 star property
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

Historic Carriage House on Washington Park. 3 Bed 2 Bath, Living Room, Kitchen

Historic Carriage House on Washington Park. 3 Bed 2 Bath, Living Room, Kitchen

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Comfortable. Homey. Very well stocked, especially the kitchen. Plenty of room and light. Thank you for our visit. "
Family-Friendly Richmond Cottage w/ Private Yard
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, (1757)
"Room was right across from the pool. Beautiful view of the mountain five min drive to the base. Beautiful pool and outdoor jacuzzi. Had an amazing stay! Cant wait to go back!"
The price is SAR 703
SAR 809 total
includes taxes & fees
23 Jan - 24 Jan
Vacation Village in the Berkshires

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is SAR 563
SAR 851 total
includes taxes & fees
26 Jan - 27 Jan
Berkshire Village Carriage House - Super Private!!
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.

Frequently asked questions

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