Default HTG hotel image

Holiday Homes in Stephentown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Stephentown holiday homes

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

1. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is AU$814
includes taxes & fees
5 Oct - 6 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

2. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is AU$298
includes taxes & fees
1 Oct - 2 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

3. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AU$335
includes taxes & fees
28 Oct - 29 Oct
1800s Carriage house in Berkshires / Hudson Valley
Pool

4. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is AU$782
includes taxes & fees
5 Oct - 6 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A white two-story house with a porch, surrounded by trees and a hill.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AU$737
includes taxes & fees
5 Oct - 6 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

6. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AU$1,580
includes taxes & fees
6 Oct - 7 Oct
Hancock Village Inn Near Jiminy Peak
A wooden deck with a table and chairs, surrounded by a white railing.

7. 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
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AU$694
includes taxes & fees
13 Oct - 14 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 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$295
includes taxes & fees
8 Oct - 9 Oct
Cozy Home in Pownal VT
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

9. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is AU$814
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A two-story house with a porch, surrounded by trees and snow.

10. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AU$459
includes taxes & fees
1 Oct - 2 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

11. 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$708
includes taxes & fees
13 Oct - 14 Oct
Treat yourself at the stunning June Farms Wellness Huts!
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is AU$483
includes taxes & fees
1 Oct - 2 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern building with a wooden deck and a door.

13. 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, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is AU$876
includes taxes & fees
5 Oct - 6 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

14. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AU$887
includes taxes & fees
1 Oct - 2 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

15. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AU$962
includes taxes & fees
25 Oct - 26 Oct
Ellie’s Overlook, best view in the Berkshires!
A kitchen with a wooden countertop, white cabinets, and red chairs. There is a staircase leading to another room.

16. Riverfront Rustic 1824 Mansion

Riverfront Rustic 1824 Mansion
Troy
9.0 out of 10, Wonderful, (14 reviews)
"Nice and very interesting property. If your into old historical properties you will love this place. Plenty of room for four adults, my grandson and our two dogs. We would stay here again. Thank You"
United States
Kevin B.
The price is AU$332
includes taxes & fees
5 Oct - 6 Oct
Riverfront Rustic 1824 Mansion
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

17. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AU$448
includes taxes & fees
1 Oct - 2 Oct
Riverside Retreat in the Berkshires
A red house with a porch, surrounded by a grassy yard and trees.

18. 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$568
includes taxes & fees
1 Oct - 2 Oct
Two Brooks Lodge
A spacious room with a wooden ceiling, large windows, and a chandelier.

19. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Retreat — All-Season Escape Awaits!
A modern kitchen with white cabinets, a wooden countertop, and a large TV mounted on the wall.

20. 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
9.8 out of 10, Exceptional, (8 reviews)
"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$535
includes taxes & fees
21 Oct - 22 Oct
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stephentown Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Very unique property. Great nostalgic atmosphere."
TAKOSHIA 1-night trip
Posted less than an hour ago
The Red Lion Inn

Find out more about Stephentown

Stephentown Holiday Homes information

Number of reviews
182
Accommodation
308 Holiday Homes
Lowest Price
AU$295
Highest Price
AU$1,580