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

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 km
Price per night
C$0
C$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
Berkshire Blueberry Lodge LLC - Near Jiminy Peak, vacation rental in Stephentown

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Meadow House 4 bdrm 4 bath house, vacation 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
A MAGIC SPOT: Booking Fall and the Ski Season now!, vacation 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
Ski Cottage in the Berkshire Hills, vacation 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, vacation 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., vacation 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
New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, vacation 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
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, vacation 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
A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, vacation 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, vacation 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
Save time - get the best Stephentown rentals sent straight to your email!
Beautiful Waterfront home with deep water dock on Onota Lake, vacation 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
Berkshire Lake House Vacation Rental, vacation 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
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, vacation rental in Stephentown

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

8 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, vacation 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
19th c. Renovated Barn in the Berkshires, vacation 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
Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak, vacation 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
Cozy renovated cabin in Williamstown, steps from hiking trails, vacation 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
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b, vacation 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
Grand Colonial Home in the Heart of The Berkshires, vacation 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, vacation 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, vacation 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
Beautiful 3 BR Berkshire Home - Mountain Views & Privacy on 10 Acres, vacation rental in Stephentown

Beautiful 3 BR Berkshire Home - Mountain Views & Privacy on 10 Acres

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
SPECTACULAR RENOVATED BERKSHIRE LAKEFRONT HOUSE ON RICHMOND POND, vacation 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
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., vacation 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, vacation 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
Morning Face - Berkshire estate with heated pool, views and privacy., vacation 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
Modern Retreat with Stunning Western Views, vacation 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
Newly renovated, spacious and sunlight filled condo with mountain views, vacation 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
Exquisite Apartment in Grand Victorian Home 1, vacation 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
6BR Berkshire Bliss - 38 private acres - close to skiing and town, vacation 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
Charming Berkshire Getaway with Scenic Lake Views & Access, vacation 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
Mounatin Getaway in the Heart of the Berkshires!, vacation 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, vacation 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, vacation rental in Stephentown

Whitman Woods - A Berkshire Vacation

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Wyndham Bentley Brook Resort, vacation rental in Stephentown

Wyndham Bentley Brook Resort

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Home in Malden Bridge, Columbia County, New York, vacation 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
Golden Triangle in the Berkshires, vacation rental in Stephentown

Golden Triangle in the Berkshires

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cedar Chest, vacation rental in Stephentown

Cedar Chest

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Christmas in The Berkshires, vacation 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, vacation 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!, vacation 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, vacation 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!, vacation 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, vacation 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, vacation 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, vacation 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!, vacation 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
Exquisite Apartment in Grand Victorian 2, vacation 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
Tentrr Signature Site - The Lodge's Campsite, vacation 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, vacation 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
Previous
12
Frequently Asked Questions about Stephentown