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Search results; Over 1,000 homes in Stephentown

Guest favourite

Flat in Stephentown

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 bedrooms, 4 beds, 1 bathroom

14–19 Jul

4.86 out of 5 average rating, 76 reviews

Guest favourite

Flat in Stephentown

Cozy 2-Bedroom Vacation Apartment

2 bedrooms, 3 beds, 1 bathroom

24–29 Aug

$1,130 SGD for 5 nights

4.99 out of 5 average rating, 107 reviews

Top guest favourite

Guest house in Stephentown

Dog Friendly Studio

1 queen bed, 1 bathroom

26–31 Jul

$1,454 SGD for 5 nights

5.0 out of 5 average rating, 476 reviews

Home in Stephentown

13BR Retreat | Heated Pool, Hot Tub + Game Room

13 bedrooms, 26 beds, 12.5 bathrooms

19–24 Jul

$12,513 SGD for 5 nights

Guest favourite

Flat in Stephentown

Berkshires Apartment @ the Stephentown Hotel

3 beds, 1 bathroom

16–21 Aug

$1,150 SGD for 5 nights

4.83 out of 5 average rating, 29 reviews

Guest favourite

Flat in Stephentown

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

5 bedrooms, 5 beds, 3 bathrooms

19–24 Jul

$2,763 SGD for 5 nights

4.88 out of 5 average rating, 17 reviews

Top guest favourite

Flat in New Lebanon

Folk Art Studio: 1-bedroom near the Berkshires

1 bedroom, 2 beds, 1 bathroom

28 Aug – 2 Sept

$863 SGD for 5 nights

5.0 out of 5 average rating, 31 reviews

Top guest favourite

Flat in New Lebanon

Airy apartment at the old boarding house

2 bedrooms, 3 beds, 1 bathroom

28 Aug – 2 Sept

$1,015 SGD for 5 nights

4.97 out of 5 average rating, 117 reviews

Top guest favourite

Holiday home in Stephentown

Quiet, peaceful wooded setting.

1 bedroom, 1 queen bed, 1 bathroom

1–6 Oct

$1,114 SGD for 5 nights

4.97 out of 5 average rating, 31 reviews

Home in Stephentown

Ioka Valley Farm's Little Farm House

3 bedrooms, 4 beds, 1 bathroom

19–24 Jul

New home discount

Free cancellation

New place to stay

Top guest favourite

Flat in New Lebanon

Loft Space above Brewery

1 bedroom, 3 beds, 1 bathroom

13–18 Sept

$1,343 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 30 reviews

Top guest favourite

Cottage in New Lebanon

The Writer's Cottage

2 bedrooms, 2 beds, 1 bathroom

31 Aug – 5 Sept

$863 SGD for 5 nights

4.94 out of 5 average rating, 214 reviews

Guest favourite

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

2 bedrooms, 3 beds, 1 bathroom

31 Aug – 5 Sept

$2,152 SGD for 5 nights

4.96 out of 5 average rating, 267 reviews

Guest favourite

Home in Stephentown

Fam-Friendly Berkshire Views and Private Swim Pond

3 bedrooms, 4 beds, 1.5 bathrooms

19–24 Jul

$3,388 SGD for 5 nights

4.89 out of 5 average rating, 35 reviews

Guest favourite

Apartment in Hancock

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

2 bedrooms, 6 beds, 2 bathrooms

18–23 Jul

$2,137 SGD for 5 nights

4.97 out of 5 average rating, 58 reviews

Guest favourite

Home in New Lebanon

Unplug in the Berkshires | Your Summer Escape

3 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$1,962 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 66 reviews

Guest favourite

Apartment in Hancock

THE SLOPE slope-view Country Inn 1BR w/heated pool

1 bedroom, 2 beds, 1 bathroom

19–24 Aug

$1,616 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Apartment in Hancock

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

3 bedrooms, 7 beds, 2 bathrooms

22–27 Jul

$2,431 SGD for 5 nights

4.94 out of 5 average rating, 99 reviews