Stephentown Vacation Rentals from ￥17,800: Search Short-Term Rentals

Q: What's the top vacation rental that Stephentown has to offer?

Berkshire Village Carriage House - Super Private!! : This vacation home rental near Stephentown is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

Check Stephentown vacation rental availability

Vacation Rentals in Stephentown

Indoor pool, outdoor pool, pool umbrellas

"Property was beautiful, great staff "

￥30,201 total

includes taxes & fees

Nov 26 - Nov 27

"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....

￥25,299 total

includes taxes & fees

Nov 26 - Nov 27

"One of the best properties i've ever stayed at "

￥34,751 total

includes taxes & fees

Dec 2 - Dec 3

"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "

"The house was very clean and the yard is large. It's a great place for family vacations."

"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."

"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "

"Very glad to have found Nana’s Place. It’s been perfect for us every time. Thank you!"

"Property was in good shape, though I recommend the owner consider refinishing the tub, the current paint job is not so good. The location is too far from downtown Troy to easily walk but is an easy drive. The building has multiple units and finding the right one was a bit tricky, but the place was clean and well-kept overall and parking was easy, I would stay again."

"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....

"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "

"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "

"Everyone enjoyed the stay"

"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"

"Great time "

￥25,415 total

includes taxes & fees

Nov 26 - Nov 27

"Beautiful, spacious house in a great location!"

"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "

"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."

"Comfortable and presentable. Location is great for going downtown or shopping in general. Restaurants are very close by. Property manager was easy to communicate with."

￥27,396 total

includes taxes & fees

Dec 1 - Dec 2

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Other types of properties in Stephentown you may be interested in

"."

￥19,047 total

includes taxes & fees

Dec 1 - Dec 2

"Great spot and just 8 minutes to downtown Albany. I had a good night sleep 😴 enjoy"

￥16,093 total

includes taxes & fees

Dec 8 - Dec 9

Hypo-allergenic bedding, laptop workspace, blackout drapes

"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "

￥20,073 total

includes taxes & fees

Dec 12 - Dec 13

Find out more about Stephentown

Search for holiday rentals in Stephentown on Expedia! You can easily find your home rentals, villas, holiday apartments in Stephentown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Stephentown!

Recent reviews of Stephentown properties

5/5 Excellent

"Beautiful room and very comfy and convenient location."

A verified traveler stayed at Life House Berkshires

Posted 1 day ago

5/5 Excellent

"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. The dinner was delicious. Plenty of seats but gave us a table facing wall (but near window) —why not more in middle of room area with more interesting view! And same table for breakfast and dinner until we requested a different table the 2nd time. Friendly service. Twin beds very comfortable better if Full size. Happy to have 2 chairs in room. Wouldn’t stay again due to bathroom issues. "

A verified traveler stayed at The Red Lion Inn

Posted 4 days ago

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent

Very good quality of towels.

"The unit was perfect in size, very good quality of towels. For the cribs, they provided new sheets and blanket that was important for us. "

A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Posted 5 days ago

Frequently asked questions

Are there vacation rentals in Stephentown?

Yes, we have vacation rentals in Stephentown close to Zema's Nursery, or you can go with a secluded option if you want a relaxing stay. Stephentown is known for its ski areas and restaurants.

What's the top vacation rental that Stephentown has to offer?

Berkshire Village Carriage House - Super Private!!: This vacation home rental near Stephentown is located in the mountains and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Stephentown?

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

What’s there to see and do in Stephentown?

While exploring the area, visit family-friendly sights like Zema's Nursery, or get outside and enjoy nature at Pittsfield State Forest. In the larger area, you’ll find Jiminy Peak Mountain Resort and Hancock Shaker Village.

What’s a vacation rental in Stephentown like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Stephentown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

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Stephentown Vacation Rentals

Check Stephentown vacation rental availability

Vacation Rentals in Stephentown

The entire Stephentown Hotel! 28 person occupancy

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Berkshire Lake access

Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library

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

3 Bedroom Lakefront Home with Hot Tub & Fireplace

Home away from home

The Kemble- Built by a US Secretary of State in Lenox

Stockbridge Home, Come Experience The Berkshires!

Chic Pittsfield Home With A View!

The Winthrop Estate - 12K SF 32 Acres

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

The Rizzy Apartment

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

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Wellspring by AvantStay | Indoor Pool + Views

2 bedroom town house with game room

Other types of properties in Stephentown you may be interested in

Hyatt Place Albany/Downtown

Comfort Inn Glenmont - Albany South

Hotel Downstreet

Find out more about Stephentown

Recent reviews of Stephentown properties

Life House Berkshires

Hilton Albany

Hyatt Place Albany

The Black Swan Lee - Lenox, Ascend Hotel Collection

Hampton Inn & Suites Albany-Downtown

Comfort Inn Glenmont - Albany South

Vacation Village in the Berkshires

The Red Lion Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Frequently asked questions