Book Holiday Homes in Stephentown

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Featured Holiday Homes in Stephentown

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA
The price is AU$432 per night from 4 Feb to 5 Feb
AU$432
4 Feb - 5 Feb
includes taxes & fees
Located in Great Barrington, this vacation home is on a river, a 4-minute walk from Monument Mountain Reservation and within a 5-minute drive of Housatonic ...
Opens in a new windowPet Friendly Riverfront Home in Great Barrington
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.
Opens in a new windowLocation!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA
With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

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

Pittsfield MA
Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.
Opens in a new windowBeautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee MA
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.
Opens in a new windowCordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Spacious 4-bedroom house with plenty of amenities in Downtown Albany

Spacious 4-bedroom house with plenty of amenities in Downtown Albany

Albany NY
With a stay at this vacation home, you'll be centrally located in Albany, a 2-minute drive from MVP Arena and 10 minutes from University at Albany.
Opens in a new windowSpacious 4-bedroom house with plenty of amenities in Downtown Albany
Berkshire House Stay

Berkshire House Stay

Lee MA
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowBerkshire House Stay
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 MA
With a stay at this vacation home in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Wyndhurst Golf & Club.
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

Stockbridge MA
With a stay at this vacation home, you'll be centrally located in Stockbridge, within a 10-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowA Grand property in Historic Stockbridge
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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
323 Holiday Homes
Lowest Price
AU$183
Highest Price
AU$432
Popular accommodation
Pet Friendly Riverfront Home in Great Barrington, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Spacious 4-bedroom house with plenty of amenities in Downtown Albany, Berkshire House Stay, Amore Estate - beautiful room with many places to explore and relax in., A Grand property in Historic Stockbridge

Top trending hotels in Stephentown

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 4 Feb to 5 Feb
AU$183
4 Feb - 5 Feb
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Opens in a new windowVacation Village in the Berkshires
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
82 MONTGOMERY STREET Albany NY
The price is AU$184 per night from 5 Mar to 6 Mar
AU$184
5 Mar - 6 Mar
includes taxes & fees
With a stay at Hyatt Place Albany/Downtown in Albany (Downtown Albany), you'll be within a 15-minute drive of MVP Arena and University at Albany.
Opens in a new windowHyatt Place Albany/Downtown
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AU$190 per night from 4 Feb to 5 Feb
AU$190
4 Feb - 5 Feb
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Opens in a new windowBerkshire Mountain Lodge
Save an average of 15% on thousands of hotels when you're signed in
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

3 out of 5
300 Broadway Albany NY
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 8 Feb to 9 Feb
AU$208
8 Feb - 9 Feb
includes taxes & fees
With a stay at Country Inn & Suites by Radisson, Downtown Albany New York in Albany (Downtown Albany), you'll be within a 15-minute drive of MVP Arena and University ...
Opens in a new windowCountry Inn & Suites by Radisson, Downtown Albany New York
Don't see what you're looking for?
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.