Book Holiday Homes in Stephentown

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Featured Holiday Homes in Stephentown

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$361 per night from 30 Dec to 31 Dec
AU$361
includes taxes & fees
30 Dec - 31 Dec
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
3 Bedroom Lakefront Home with Hot Tub & Fireplace

3 Bedroom Lakefront Home with Hot Tub & Fireplace

Wynantskill
Located in Wynantskill, this vacation home is on the waterfront, within a 10-minute drive of Kinloch Park Dog Park and Joseph L Bruno Stadium.
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.
Amore Estate - beautiful room with many places to explore and relax in.
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox
Located in Lenox, this vacation home is within a 15-minute walk of Pleasant Valley Wilderness Sanctuary and Kennedy Park.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

Stockbridge
A stay at this vacation home places you in the heart of Stockbridge, steps from Housatonic River and Mission House.
A Grand property in Historic Stockbridge
Berkshire Ashmere Lake lodging. Quiet  room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
With a stay at this vacation home in Hinsdale, you'll be within a 15-minute drive of Bas Ridge Golf Course and Crane Museum of Papermaking.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hudson Valley and The Berkshires getaway

Hudson Valley and The Berkshires getaway

Hillsdale
Located in Hillsdale, this vacation home is within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Hillsdale Town Hall.
Hudson Valley and The Berkshires getaway
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

Pownal
With a stay at this vacation home in Pownal, you'll be steps from Green Mountain National Forest and a 3-minute drive from Mountain Meadow Preserve.
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

Pittsfield
When you stay at this vacation home in Pittsfield, you'll be near the beach, within a 5-minute drive of Housatonic River and Guido's Marketplace.
Chic Pittsfield Home With A View!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stephentown Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Stephentown vacation homes are the perfect way for you to wing it.

Holiday houses in Stephentown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Stephentown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Stephentown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Stephentown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Stephentown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Stephentown Holiday Homes essential information

Accommodation
260 Holiday Homes
Lowest Price
AU$176
Highest Price
AU$361
Popular accommodation
Berkshire Village Carriage House - Super Private!!, 3 Bedroom Lakefront Home with Hot Tub & Fireplace, Amore Estate - beautiful room with many places to explore and relax in., Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, A Grand property in Historic Stockbridge, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Hudson Valley and The Berkshires getaway, Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!, Chic Pittsfield Home With A View!

Top trending hotels in Stephentown

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
82 MONTGOMERY STREET, Albany, NY
Fully refundableReserve now, pay when you stay
The price is AU$218 per night from 29 Dec to 30 Dec
AU$218
includes taxes & fees
29 Dec - 30 Dec
With a stay at Hyatt Place Albany/Downtown in Albany (Downtown Albany), you'll be within a 15-minute drive of University at Albany and Colonie Center Mall.
Hyatt Place Albany/Downtown
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
25 Chapel St, Albany, NY
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 29 Dec to 30 Dec
AU$215
includes taxes & fees
29 Dec - 30 Dec
With a stay at Hampton Inn & Suites Albany-Downtown, you'll be centrally located in Albany, within a 15-minute drive of University at Albany and Colonie Center ...
Hampton Inn & Suites Albany-Downtown
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundable
The price is AU$176 per night from 2 Jan to 3 Jan
AU$176
includes taxes & fees
2 Jan - 3 Jan 2025
A stay at Comfort Inn Glenmont - Albany South places you in the heart of Glenmont, within a 10-minute drive of MVP Arena and Albany Capital Center.
Comfort Inn Glenmont - Albany South
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Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 5 Jan to 6 Jan
AU$207
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum ...
Hotel Downstreet
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See all available properties in Stephentown
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.