Stephentown Vacation Rentals

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Check prices for these dates

Tonight
Mar 3 - Mar 4
Tomorrow
Mar 4 - Mar 5
This weekend
Mar 7 - Mar 9
Next weekend
Mar 14 - Mar 16

Vacation Rentals in Stephentown

Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

The price is ￥14,460
￥34,596 total
includes taxes & fees
Mar 4 - Mar 5
Charming 3-bedroom Cabin for nature lovers
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1779)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"
The price is ￥16,419
￥19,517 total
includes taxes & fees
Mar 4 - Mar 5
Vacation Village in the Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is ￥22,444
￥24,621 total
includes taxes & fees
Apr 1 - Apr 2
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is ￥22,595
￥34,325 total
includes taxes & fees
Mar 4 - Mar 5
Berkshire Village Carriage House - Super Private!!
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

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

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is ￥90,077
￥159,877 total
includes taxes & fees
Mar 4 - Mar 5
Hancock Village Inn at Jiminy Peak
BEAUTIFUL ESTATE! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES
Fridge, microwave, oven, stovetop

BEAUTIFUL ESTATE! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
BEAUTIFUL ESTATE! POOL, POND, ARCADE, GYM, TRAILS, BARN! ASK ABOUT REDUCED RATES
Chic Madison Parkview
Fridge, microwave, oven, stovetop

Chic Madison Parkview

10.0 out of 10, Exceptional, (12)
"Close to a lot of local businesses and was a cute apartment. Would stay here again. "
The price is ￥14,912
￥26,059 total
includes taxes & fees
Mar 4 - Mar 5
Chic Madison Parkview
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

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

10.0 out of 10, Exceptional, (119)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Cabin in the woods
Exterior

Cabin in the woods

10.0 out of 10, Exceptional, (9)
"This place was awesome... I was 15 minutes away working late... and I was too tired to drive home... I actually scheduled the wrong night and realized it after I got confirmation. But I messaged the renters and they just happened to have a cabin vacancy... they gave me the directions.. the key code and we worked everything out afterwards. The set-up is genius... the common area building has all the plumbing in it. Bathroom and showers with an open very well built living room with a kitchen. My...
The price is ￥18,076
￥25,547 total
includes taxes & fees
Mar 4 - Mar 5
Cabin in the woods
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
Smart TV, fireplace, DVD player, books

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

9.6 out of 10, Exceptional, (29)
"We had a very peaceful and relaxing stay. The atmosphere was quiet and calming, perfect for unwinding. Everything about our time here was enjoyable, and we truly appreciated the serene environment. Highly recommend it for anyone looking for a restful getaway! "
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
Private Access To Laurel Lake, Enjoy Lake Life
Outdoor dining

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
Fridge, microwave, oven, stovetop

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

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

9.6 out of 10, Exceptional, (7)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (19)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakeside Retreat Just You, The Lake & The View!
Exterior

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (69)
"We had a lovely stay. Views are amazing. Property owner was very responsive and helpful. Would love to go back in the fall."
Lakeside Retreat Just You, The Lake & The View!
Secluded Lux Mansion Pool Home with Amazing Views
Fridge, microwave, oven, stovetop

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views
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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Other types of properties in Stephentown you may be interested in

Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

The price is ￥14,460
￥34,596 total
includes taxes & fees
Mar 4 - Mar 5
Charming 3-bedroom Cabin for nature lovers
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1779)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"
The price is ￥16,419
￥19,517 total
includes taxes & fees
Mar 4 - Mar 5
Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection
Indoor spa tub

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1002)
"Great spot to break the drive up between CT and VT. "
The price is ￥17,797
￥19,879 total
includes taxes & fees
Mar 16 - Mar 17
Hotel Downstreet, Ascend Hotel Collection
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.

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?

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

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.