Stephentown Holiday Homes from £158: Search Holiday Homes in Stephentown

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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

Stephentown

Robert B.

includes taxes & fees

1 Nov - 2 Nov

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 Lebanon

Joanna P.

includes taxes & fees

29 Oct - 30 Oct

A spacious living room with a dining area, a kitchen, and a large window.

3. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

includes taxes & fees

5 Nov - 6 Nov

4. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

includes taxes & fees

29 Oct - 30 Oct

A white two-story house with a porch, surrounded by trees and a hill.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

includes taxes & fees

9 Nov - 10 Nov

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

Price F.

includes taxes & fees

17 Nov - 18 Nov

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!

Pittsfield

Stephen L.

includes taxes & fees

29 Oct - 30 Oct

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Pownal

Jeri R.

includes taxes & fees

29 Oct - 30 Oct

A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

9. Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

Lauren C.

includes taxes & fees

3 Nov - 4 Nov

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

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

Williamstown

Michelle B.

includes taxes & fees

29 Oct - 30 Oct

A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

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

Richmond

"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...

Delaney M.

includes taxes & fees

2 Nov - 3 Nov

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

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

New Lebanon

Anonymous traveller

includes taxes & fees

9 Nov - 10 Nov

A modern building with a wooden deck and a door.

13. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

includes taxes & fees

29 Oct - 30 Oct

A room with a large window, two sofas, and a small table.

14. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Richmond

includes taxes & fees

30 Oct - 31 Oct

A cozy living room with a sofa, a fireplace, and large windows.

15. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

includes taxes & fees

29 Oct - 30 Oct

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

Chatham

Jess S.

includes taxes & fees

29 Oct - 30 Oct

A kitchen with white cabinets, a wooden dining table, and pendant lights.

17. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

includes taxes & fees

30 Oct - 31 Oct

A kitchen with a wooden countertop, white cabinets, and red chairs. There is a staircase leading to another room.

18. Riverfront Rustic 1824 Mansion

Troy

Alex V.

includes taxes & fees

2 Nov - 3 Nov

A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

19. Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

SteveS

includes taxes & fees

3 Nov - 4 Nov

A wooden cabin with a curved roof, two windows, and a door, surrounded by a garden and forest.

20. June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

West Sand Lake

LauraS

includes taxes & fees

2 Nov - 3 Nov

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Top Stephentown Hotel Reviews

The Yankee Inn

8/10 Good

"We stayed at the Yankee Inn for 1 night. We had no problems with check-in. Our room was clean but outdated except the bathroom which was very nice. Good water pressure in the shower and the bed was comfortable. Unfortunately, due to myself not feeling well, we did not use the hot tub, enjoy the fire pit or try breakfast all of which would have likely improved our stay. Maybe next time!"