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Over 1,000 places in Stephentown

Guest favorite

Apartment in Stephentown

Berkshires Apartment @ the Stephentown Hotel

3 beds

Apr 20 – 25

$105 per night

4.83 out of 5 average rating, 6 reviews

Guest favorite

Farm stay in Stephentown

Private Historic Farmhouse- 5 mins to Jiminy Peak

8 beds

Apr 20 – 25

$425 per night

4.87 out of 5 average rating, 30 reviews

Guest favorite

Apartment in Stephentown

2 Bed Berkshire Getaway @ Stephentown Hotel

4 beds

May 9 – 14

$150 per night

4.92 out of 5 average rating, 26 reviews

Guest favorite

Apartment in Stephentown

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

5 beds

Apr 20 – 25

$286 per night, originally $337

4.88 out of 5 average rating, 8 reviews

Guest favorite

Guesthouse in Stephentown

Dog Friendly Studio

1 queen bed

Apr 21 – 26

$185 per night

5.0 out of 5 average rating, 359 reviews

Guest favorite

Home in Stephentown

Secluded Berkshire home-foliage/Ski

4 beds

Apr 23 – 28

$299 per night

5.0 out of 5 average rating, 11 reviews

Guest favorite

Apartment in Stephentown

Cozy 2-Bedroom Vacation Apartment

3 beds

May 5 – 10

$120 per night

5.0 out of 5 average rating, 50 reviews

Superhost

Cabin in Stephentown

Cabin in the woods w cedar Hot Tub + private pond

2 queen beds

Apr 25 – 30

$224 per night, originally $265

4.84 out of 5 average rating, 236 reviews

Guest favorite

Vacation home in Stephentown

Quiet, peaceful wooded setting.

1 queen bed

Apr 28 – May 3

$95 per night

4.94 out of 5 average rating, 17 reviews

Guest favorite

Home in Stephentown

Berkshire Cabin

1 bed

Apr 20 – 25

$210 per night

5.0 out of 5 average rating, 7 reviews

Guest favorite

Guest suite in Hancock

Cozy apartment near Jiminy Peak

3 beds

Apr 21 – 26

$72 per night

4.83 out of 5 average rating, 154 reviews

Home in Stephentown

A Magic Spot: Booking year round.

5 beds

Apr 22 – 27

$200 per night

4.81 out of 5 average rating, 63 reviews

Superhost

Home in Hancock

Woodland 5-BR Retreat 5-Min to Jiminy Peak

6 beds

Apr 20 – 25

$175 per night, originally $384

New place to stay

Guest favorite

Farm stay in New Lebanon

Barn Stay at Shadowbrook Farm

3 beds

Apr 21 – 26

$176 per night, originally $200

4.95 out of 5 average rating, 184 reviews

Guest favorite

Condo in Hancock

Jiminy Peak Country Inn - ski in/out condo MT view

1 king bed

Apr 21 – 26

$99 per night

4.9 out of 5 average rating, 51 reviews

Guest favorite

Apartment in Petersburg

The Beer Diviner Brewery Apartment

2 beds

Jun 2 – 7

$75 per night

4.85 out of 5 average rating, 147 reviews

Guest favorite

Yurt in Stephentown

Off Grid Yurt Right By The Best of The Berkshires

2 beds

Apr 21 – 26

$111 per night

4.91 out of 5 average rating, 89 reviews

Guest favorite

Home in Lebanon Springs

Summer Getaway: Historic Home Near Tanglewood

3 beds

Apr 21 – 26

$133 per night

4.92 out of 5 average rating, 73 reviews