Holiday Homes in Stephentown

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Our top choices for Stephentown holiday homes

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$783
includes taxes & fees
17 May - 18 May
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"We had a great family getaway here! The hot tub was amazing and the views from the hot tub were perfect. What a beautiful location - quiet, peaceful and a fun space for kids to explore. We had an amazing time trekking out in the woods in the snow.Kitchen was well stocked and the treats, coffee and tea were a nice bonus. My kids enjoyed the extra games as well! Extremely quick responses from the host as well! Thanks for a good time, we are already thinking about coming back in the summer."
United States
Amanda H.
The price is AU$420
includes taxes & fees
18 May - 19 May
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$615
includes taxes & fees
18 May - 19 May
North Getaway Cottage

Riverfront Rustic 1824 Mansion

Riverfront Rustic 1824 Mansion
Troy
8.8 out of 10, Excellent, (8 reviews)
"Loved the house! So much character and in a great location! "
United States
Alex V.
The price is AU$338
includes taxes & fees
20 May - 21 May
Riverfront Rustic 1824 Mansion

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AU$286
includes taxes & fees
17 May - 18 May
Cozy Home in Pownal VT

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is AU$525
includes taxes & fees
18 May - 19 May
Near Tanglewood: Historic Summer Retreat

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AU$669
includes taxes & fees
24 May - 25 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is AU$552
includes taxes & fees
17 May - 18 May
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is AU$439
includes taxes & fees
20 May - 21 May
Cozy Riverside Berkshires Retreat

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is AU$668
includes taxes & fees
18 May - 19 May
Treat yourself at the stunning June Farms Wellness Huts!

Perfect 4-bedroom house with AC in tranquil Albany

Perfect 4-bedroom house with AC in tranquil Albany
Delaware Avenue
The price is AU$759
includes taxes & fees
25 May - 26 May
Perfect 4-bedroom house with AC in tranquil Albany

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is AU$757
includes taxes & fees
17 May - 18 May
Comfortable Berkshires retreat on mtn resort, SISO

Downtown 3BR duplex full kitchen parking off i-787

Downtown 3BR duplex full kitchen parking off i-787
Arbor Hill
10.0 out of 10, Exceptional, (5 reviews)
"The owners gave us fresh baked bread - twice. Also helped us get parking in a location with very few spots. Real nice owners for this property and would come back any time! "
United States
Victor
The price is AU$432
includes taxes & fees
19 May - 20 May
Downtown 3BR duplex full kitchen parking off i-787

Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Pine Hills
10.0 out of 10, Exceptional, (1 review)
"The house was nicely setup and clean. The location was very central to where we needed to be. The host was very responsive. "
United States
Elizabeth P.
The price is AU$531
includes taxes & fees
18 May - 19 May
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

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

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AU$1,064
includes taxes & fees
18 May - 19 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (6 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is AU$557
includes taxes & fees
8 June - 9 June
The Greylock Cabin

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (4 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AU$452
includes taxes & fees
18 May - 19 May
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (1 review)
"My family and I had a lovely stay at Oscar’s Pond Estate! The house was clean and inviting, and provided everything we needed for a comfortable stay. The surrounding area provided beautiful views as we enjoyed the back deck and yard, complete with a hot tub and fire pit. I highly recommend the nearby Art Omi sculpture park if you stay here. It was a perfect outing for our 2 families with 4 kids ages 2 to 9. The owner was incredibly warm and responsive and provided clear and easy check-in...
United States
Betsy H.
The price is AU$884
includes taxes & fees
18 May - 19 May
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is AU$573
includes taxes & fees
17 May - 18 May
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is AU$545
includes taxes & fees
18 May - 19 May
Two Brooks Lodge
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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Top Stephentown Hotel Reviews

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Stephentown Holiday Homes information

Number of reviews
206
Accommodation
314 Holiday Homes
Lowest Price
AU$286
Highest Price
AU$1,064