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 Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
51 rentals in Stephentown.
Sort by:
Tripadvisor Sort
A MAGIC SPOT: Booking Fall and the Ski Season now!, holiday rental in Stephentown

A MAGIC SPOT: Booking Fall and the Ski Season now!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Meadow House 4 bdrm 4 bath house, holiday rental in Stephentown

The Meadow House 4 bdrm 4 bath house

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Ski Cottage in the Berkshire Hills, holiday rental in Stephentown

Ski Cottage in the Berkshire Hills

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Berkshire Village Carriage House, holiday rental in Stephentown

Berkshire Village Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Recently renovated 4 bedroom lakefront house in The Berkshires., holiday rental in Stephentown

Recently renovated 4 bedroom lakefront house in The Berkshires.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, holiday rental in Stephentown

Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, holiday rental in Stephentown

New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, holiday rental in Stephentown

A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Tranquil Lake House Getaway on Onota Lake, holiday rental in Stephentown

Tranquil Lake House Getaway on Onota Lake

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Berkshire Lake House Vacation Rental, holiday rental in Stephentown

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Stephentown rentals sent straight to your email!
Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, holiday rental in Stephentown

Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Waterfront home with deep water dock on Onota Lake, holiday rental in Stephentown

Beautiful Waterfront home with deep water dock on Onota Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cozy renovated cabin in Williamstown, steps from hiking trails, holiday rental in Stephentown

Cozy renovated cabin in Williamstown, steps from hiking trails

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
19th c. Renovated Barn in the Berkshires, holiday rental in Stephentown

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, holiday rental in Stephentown

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak, holiday rental in Stephentown

Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Grand Colonial Home in the Heart of The Berkshires, holiday rental in Stephentown

Grand Colonial Home in the Heart of The Berkshires

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Home in the Berkshires, holiday rental in Stephentown

Home in the Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly Renovated Waterfront Lakehouse for rent, holiday rental in Stephentown

Newly Renovated Waterfront Lakehouse for rent

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., holiday rental in Stephentown

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, holiday rental in Stephentown

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, holiday rental in Stephentown

SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Home in Malden Bridge, Columbia County, New York, holiday rental in Stephentown

The Home in Malden Bridge, Columbia County, New York

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautifully decorated with holiday lights and tree, holiday rental in Stephentown

Beautifully decorated with holiday lights and tree

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Modern Retreat with Stunning Western Views, holiday rental in Stephentown

Modern Retreat with Stunning Western Views

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Morning Face - Berkshire estate with heated pool, views and privacy., holiday rental in Stephentown

Morning Face - Berkshire estate with heated pool, views and privacy.

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Exquisite Apartment in Grand Victorian Home 1, holiday rental in Stephentown

Exquisite Apartment in Grand Victorian Home 1

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Gathering at High Mowing Williamstown, holiday rental in Stephentown

The Gathering at High Mowing Williamstown

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming Berkshire Getaway with Scenic Lake Views & Access, holiday rental in Stephentown

Charming Berkshire Getaway with Scenic Lake Views & Access

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly renovated, spacious and sunlight filled condo with mountain views, holiday rental in Stephentown

Newly renovated, spacious and sunlight filled condo with mountain views

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
6BR Berkshire Bliss - 38 private acres - close to skiing and town, holiday rental in Stephentown

6BR Berkshire Bliss - 38 private acres - close to skiing and town

6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Mounatin Getaway in the Heart of the Berkshires!, holiday rental in Stephentown

Mounatin Getaway in the Heart of the Berkshires!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, holiday rental in Stephentown

Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Whitman Woods - A Berkshire Vacation, holiday rental in Stephentown

Whitman Woods - A Berkshire Vacation

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Golden Triangle in the Berkshires, holiday rental in Stephentown

Golden Triangle in the Berkshires

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Bentley/Wyndham Hancock Mass at Jiminy Peak, holiday rental in Stephentown

Bentley/Wyndham Hancock Mass at Jiminy Peak

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Exquisite Apartment in Grand Victorian 2, holiday rental in Stephentown

Exquisite Apartment in Grand Victorian 2

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Christmas in The Berkshires, holiday rental in Stephentown

Christmas in The Berkshires

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Thanksgiving week lux condo/4 Berkshires, holiday rental in Stephentown

Thanksgiving week lux condo/4 Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, holiday rental in Stephentown

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, holiday rental in Stephentown

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, holiday rental in Stephentown

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Berkshire Mountain Hideaway, holiday rental in Stephentown

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Center Berlin Campsite, holiday rental in Stephentown

Tentrr Signature Site - Center Berlin Campsite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Round Mountain Camp, holiday rental in Stephentown

Tentrr Signature Site - Round Mountain Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, holiday rental in Stephentown

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - The Lodge's Campsite, holiday rental in Stephentown

Tentrr Signature Site - The Lodge's Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Apartment Newly Remodeled Super Location, holiday rental in Stephentown

Apartment Newly Remodeled Super Location

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
NEW! Lakeside Berkshires Home Near Hiking & Skiing, holiday rental in Stephentown

NEW! Lakeside Berkshires Home Near Hiking & Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Brookman - Newly Renovated 6,000 SF Estate on 40 Acres, holiday rental in Stephentown

The Brookman - Newly Renovated 6,000 SF Estate on 40 Acres

8 bedrooms
6 bathrooms
Sleeps 25
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Previous
12
Frequently Asked Questions about Stephentown