Holiday Rentals in Stephentown

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Holiday Rentals in Stephentown

Cabin in Stephentown

7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is €284
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom Cabin for nature lovers

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2138)
"Great place!"
United States
Nicole
The price is €81
includes taxes & fees
23 Nov - 24 Nov
Vacation Village in the Berkshires

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is €144
includes taxes & fees
25 Nov - 26 Nov
Jiminy Peak Mountain Resort

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is €183
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
The price is €123
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow

Apartment in Washington Square

7.2 out of 10, Good, (10)
"Antonio made our stay a great experience from start to finish. He was friendly, responsive, and made everything so convenient for us. The place was exactly what we needed—clean, comfortable, and in a great location.Check-in and check-out were smooth, and Antonio made sure we had everything we needed for a stress-free stay. You can really tell he cares about his guests and puts thought into making it a welcoming space.Highly recommend booking with Antonio—would definitely stay again!"
United States
Kira C.
The price is €180
includes taxes & fees
23 Nov - 24 Nov
The Rizzy Apartment

Cabin in Sand Lake

10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is €164
includes taxes & fees
22 Nov - 23 Nov
Taborton Harvest Boulder Pines Cabin in the woods

Holiday Home in Great Barrington

9.2 out of 10, Wonderful, (5)
The price is €262
includes taxes & fees
23 Nov - 24 Nov
Pet Friendly Riverfront Home in Great Barrington

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox

Apartment in Hudson Park

8.8 out of 10, Excellent, (26)
"The apartment is very cozy, spacious and discreet. Perfect if your just looking for something that’s not too in the open. "
United States
D’Andre D.
The price is €161
includes taxes & fees
24 Nov - 25 Nov
NEW Cozy Apt Bright + Modern W/D

Holiday Home in Lee

8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is €702
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi

Apartment in Albany

9.6 out of 10, Exceptional, (31)
"Location close to restaurants and parks."
United States
Alex B.
The price is €156
includes taxes & fees
22 Nov - 23 Nov
Chic Madison Parkview

Holiday Home in Hancock

10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is €989
includes taxes & fees
9 Dec - 10 Dec
Hancock Village Inn Near Jiminy Peak

Holiday Home in Old Chatham

9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Apartment in Albany

2.0 star property
8.0 out of 10, Very good, (2)
"The building and apartment are dated but very adequate for a studio apartment. Comfortable bed. The neighborhood is great. "
United States
Larry B.
The price is €159
includes taxes & fees
23 Nov - 24 Nov
Safe Sweet Serene - Empire Plaza

Holiday Home in Stockbridge

10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Holiday Home in Pittsfield

9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Apartment in Lee

9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Holiday Home in Hinsdale

9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Holiday Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is €653
includes taxes & fees
8 Dec - 9 Dec
Comfortable Berkshires retreat on mtn resort, SISO
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.
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Top Stephentown Hotel Reviews

Find out more about Stephentown

Everything you need to know about Stephentown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stephentown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stephentown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stephentown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stephentown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stephentown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stephentown holiday rentals we have selected for you start as low as €81 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stephentown rentals

At Expedia, we put the best Stephentown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Stephentown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stephentown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stephentown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Stephentown?

Yes, there are holiday rentals in Stephentown close to Zema's Nursery, or you can select a more secluded option if you're looking for a relaxing stay. Stephentown is known for its ski areas and restaurants.

What are some of the best holiday rentals that Stephentown has to offer?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Stephentown is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Stephentown?

Choose from 6 Expedia holiday rentals in Stephentown for a memorable holiday.

What’s there to see and do in Stephentown?

Family-friendly attractions include Zema's Nursery, whereas Taconic Ridge State Forest is a spot to enjoy the outdoors. In the wider area, you’ll find Jiminy Peak Mountain Resort and Hancock Shaker Village.

What’s a holiday rental in Stephentown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stephentown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.