We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Stephentown Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
51 rentals in Stephentown.
Private country home minutes from the Berkshires, vacation rental in Stephentown
Private country home minutes from the Berkshires, vacation rental in Stephentown
Private country home minutes from the Berkshires, vacation rental in Stephentown

Private country home minutes from the Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Stephentown Hotel!, vacation rental in Stephentown
The Stephentown Hotel!, vacation rental in Stephentown
The Stephentown Hotel!, vacation rental in Stephentown

The Stephentown Hotel!

Private Room
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond, vacation rental in Stephentown
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond, vacation rental in Stephentown
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond, vacation rental in Stephentown

Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ, vacation rental in Stephentown
2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ, vacation rental in Stephentown
2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ, vacation rental in Stephentown

2 Bed Berkshire Getaway minutes to Jiminy Peak! Stephentown Hotel w/ Firepit BBQ

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt., vacation rental in Stephentown
2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt., vacation rental in Stephentown
2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt., vacation rental in Stephentown

2 Bed Berkshire Getaway * Stephentown Hotel! Minutes to Jiminy Peak! 2nd FL Apt.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Farm House in Mt. Meadow, vacation rental in Stephentown
Farm House in Mt. Meadow, vacation rental in Stephentown
Farm House in Mt. Meadow, vacation rental in Stephentown

Farm House in Mt. Meadow

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available, vacation rental in Stephentown
A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available, vacation rental in Stephentown
A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available, vacation rental in Stephentown

A MAGIC SPOT: Booking spring and summer. Weekly, monthly discounts available

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq., vacation rental in Stephentown
Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq., vacation rental in Stephentown
Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq., vacation rental in Stephentown

Stephentown Hotel Triplex 5 bedroom. Minutes to Jiminy Peak. Plus firepit & bbq.

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
WE'RE OPEN AGAIN FOR IMMUNIZED FOLKS AND THEIR PETS, vacation rental in Stephentown
WE'RE OPEN AGAIN FOR IMMUNIZED FOLKS AND THEIR PETS, vacation rental in Stephentown
WE'RE OPEN AGAIN FOR IMMUNIZED FOLKS AND THEIR PETS, vacation rental in Stephentown

WE'RE OPEN AGAIN FOR IMMUNIZED FOLKS AND THEIR PETS

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Ski Cottage in the Berkshire Hills, vacation rental in Stephentown
Ski Cottage in the Berkshire Hills, vacation rental in Stephentown
Ski Cottage in the Berkshire Hills, vacation rental in Stephentown

Ski Cottage in the Berkshire Hills

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
The Meadow House 4 bdrm 4 bath house , vacation rental in Stephentown
The Meadow House 4 bdrm 4 bath house , vacation rental in Stephentown
The Meadow House 4 bdrm 4 bath house , vacation rental in Stephentown

The Meadow House 4 bdrm 4 bath house

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
The following properties within 20 miles of Stephentown match all your filters:
Ski-In/Ski-Out at Jiminy Peak  in the Country Inn, vacation rental in Stephentown
Ski-In/Ski-Out at Jiminy Peak  in the Country Inn, vacation rental in Stephentown
Ski-In/Ski-Out at Jiminy Peak  in the Country Inn, vacation rental in Stephentown

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Ski season is here!, vacation rental in Stephentown
Ski season is here!, vacation rental in Stephentown
Ski season is here!, vacation rental in Stephentown

Ski season is here!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn, vacation rental in Stephentown
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn, vacation rental in Stephentown
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn, vacation rental in Stephentown

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautifully Renovated Condo, vacation rental in Stephentown
Beautifully Renovated Condo, vacation rental in Stephentown
Beautifully Renovated Condo, vacation rental in Stephentown

Beautifully Renovated Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Recently Updated Condo at Jiminy Peak, vacation rental in Stephentown
Recently Updated Condo at Jiminy Peak, vacation rental in Stephentown
Recently Updated Condo at Jiminy Peak, vacation rental in Stephentown

Recently Updated Condo at Jiminy Peak

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base, vacation rental in Stephentown
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base, vacation rental in Stephentown
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base, vacation rental in Stephentown

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!, vacation rental in Stephentown
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!, vacation rental in Stephentown
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!, vacation rental in Stephentown

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Stephentown
Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Stephentown
Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak., vacation rental in Stephentown

Quiet & private small horse farm with mountain views. 1.5 miles to Jiminy Peak.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
UNIQUE  Themed- 1BR Country Condo * Jiminy Peak, vacation rental in Stephentown
UNIQUE  Themed- 1BR Country Condo * Jiminy Peak, vacation rental in Stephentown
UNIQUE  Themed- 1BR Country Condo * Jiminy Peak, vacation rental in Stephentown

UNIQUE Themed- 1BR Country Condo * Jiminy Peak

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Hancock Village Inn at Jiminy Peak, vacation rental in Stephentown
Hancock Village Inn at Jiminy Peak, vacation rental in Stephentown
Hancock Village Inn at Jiminy Peak, vacation rental in Stephentown

Hancock Village Inn at Jiminy Peak

Rental Home
7 bedrooms
6 bathrooms
Sleeps 17
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Mountainside Condo at Jiminy Peak in the Berkshires, vacation rental in Stephentown
Mountainside Condo at Jiminy Peak in the Berkshires, vacation rental in Stephentown
Mountainside Condo at Jiminy Peak in the Berkshires, vacation rental in Stephentown

Mountainside Condo at Jiminy Peak in the Berkshires

Rental Home
2 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Stephentown
Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Stephentown
Vacation Village in the Berkshires - 1 Bedroom, vacation rental in Stephentown

Vacation Village in the Berkshires - 1 Bedroom

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming 18th century Farmhouse; only 1.5 miles to Jiminy Peak, vacation rental in Stephentown
Charming 18th century Farmhouse; only 1.5 miles to Jiminy Peak, vacation rental in Stephentown
Charming 18th century Farmhouse; only 1.5 miles to Jiminy Peak, vacation rental in Stephentown

Charming 18th century Farmhouse; only 1.5 miles to Jiminy Peak

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Private Country home near Berkshires, vacation rental in Stephentown
Private Country home near Berkshires, vacation rental in Stephentown
Private Country home near Berkshires, vacation rental in Stephentown

Private Country home near Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!, vacation rental in Stephentown
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!, vacation rental in Stephentown
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!, vacation rental in Stephentown

Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Ski on ski off 1 Br loft condo in the village center with private gated parking, vacation rental in Stephentown
Ski on ski off 1 Br loft condo in the village center with private gated parking, vacation rental in Stephentown
Ski on ski off 1 Br loft condo in the village center with private gated parking, vacation rental in Stephentown

Ski on ski off 1 Br loft condo in the village center with private gated parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!, vacation rental in Stephentown
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!, vacation rental in Stephentown
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!, vacation rental in Stephentown

1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Full Week of Ski-in,Ski-out * Jiminy Peak Club Whyndam Bently Brook in Berkshire, vacation rental in Stephentown
Full Week of Ski-in,Ski-out * Jiminy Peak Club Whyndam Bently Brook in Berkshire, vacation rental in Stephentown
Full Week of Ski-in,Ski-out * Jiminy Peak Club Whyndam Bently Brook in Berkshire, vacation rental in Stephentown

Full Week of Ski-in,Ski-out * Jiminy Peak Club Whyndam Bently Brook in Berkshire

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
WEEKEND FUN, vacation rental in Stephentown
WEEKEND FUN, vacation rental in Stephentown
WEEKEND FUN, vacation rental in Stephentown

WEEKEND FUN

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Showing results 1-30 of 51
Frequently Asked Questions about Stephentown