Book Holiday Homes in Stephentown

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Stephentown

Home away from home

Home away from home

Troy
Located in Troy, this vacation home is within a 15-minute drive of MVP Arena and Albany Medical Center.
Home away from home
Gorgeous 3BR 3BA Sleeps 10  Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
The price is AU$826 per night from 24 Nov to 25 Nov
AU$826
includes taxes & fees
24 Nov - 25 Nov
With a stay at this vacation home, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!

Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!

Rensselaer
Located in Rensselaer, this vacation home is in a rural location, a 5-minute drive from Hudson River and 6 minutes from Palace Theater.
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Save an average of 15% on thousands of hotels when you're signed in
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.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
The price is AU$794 per night from 1 Dec to 2 Dec
AU$794
includes taxes & fees
1 Dec - 2 Dec
Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge
Located in South Lee, this vacation home is in a rural location, within a 5-minute drive of Berkshire Botanical Garden and Housatonic River.
Secluded Family Home in Serene Stockbridge Woods
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$343 per night from 25 Nov to 26 Nov
AU$343
includes taxes & fees
25 Nov - 26 Nov
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!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Berkshire Botanical Garden and Tanglewood Music Center.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Adams
A stay at this vacation home places you in the heart of Adams, steps from Mount Greylock State Reservation and 7 minutes by foot from East Hoosac Quaker ...
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Don't see what you're looking for?
See all available properties in Stephentown
View all properties
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
249 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$826
Popular accommodation
Home away from home, Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Cozy Cape Close to Everything: Family, hiking, shopping and restaurants! , Amore Estate - beautiful room with many places to explore and relax in., Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Secluded Family Home in Serene Stockbridge Woods, Berkshire Village Carriage House - Super Private!!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Top trending hotels in Stephentown

Hyatt Place Albany

Hyatt Place Albany

3 out of 5
82 MONTGOMERY STREET, Albany, NY
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 1 Dec to 2 Dec
AU$189
includes taxes & fees
1 Dec - 2 Dec
With a stay at Hyatt Place Albany/Downtown in Albany (Downtown Albany), you'll be within a 5-minute drive of MVP Arena and Albany Medical Center.
Hyatt Place Albany
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 8 Dec to 9 Dec
AU$160
includes taxes & fees
8 Dec - 9 Dec
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
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$199 per night from 5 Dec to 6 Dec
AU$199
includes taxes & fees
5 Dec - 6 Dec
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
Save an average of 15% on thousands of hotels when you're signed in
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$174 per night from 8 Dec to 9 Dec
AU$174
includes taxes & fees
8 Dec - 9 Dec
With a stay at Hampton Inn & Suites Albany-Downtown, you'll be centrally located in Albany, within a 5-minute drive of MVP Arena and Albany Medical Center.
Hampton Inn & Suites Albany-Downtown
Don't see what you're looking for?
See all available properties in Stephentown
View all properties
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.