Holiday Rentals in Stephentown

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Holiday Rentals in Stephentown

Private country home minutes from the Berkshires
5.4 out of 10, 11 reviews
"Do not stay here! I am an international traveler, backpacker, and am used to some rough accommodations, but this stay was truly awful. My friend and I booked the space for a weekend, despite reading the previous reviews, thinking it could not be that bad. The house was overwhelmingly musty, there was mold up into the windowsills, the carpeting felt damp to walk on, and least of all the beds were hard and uncomfortable. We left after one night. It felt like a health hazard to be there. Neither...
The price is €191
per night
5 Jun - 6 Jun
Private country home minutes from the Berkshires
The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, 858 reviews
"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"
The price is €160
per night
5 Jun - 6 Jun
Jiminy Peak Mountain Resort
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Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, 2 reviews
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Home away from home
10.0 out of 10, Exceptional, 5 reviews
"nice and quiet location. Close to alot of good food places. Great location for the things we came to do."
Home away from home
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, 39 reviews
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, 205 reviews
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, 97 reviews
"Lovely chalet by the lake, we had such a relaxing stay. The place is just like on the pictures, very quiet but not far from amenities. The host are very friendly super responsive. Thanks for having us!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, 12 reviews
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, 15 reviews
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Berkshire Lake access
10.0 out of 10, Exceptional, 41 reviews
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
9.6 out of 10, Exceptional, 79 reviews
"We had 4 families and grandparents all stay together for an unforgettable weekend at Bellavista. The house had enough space for us to hang out together playing charades in the great room, ping pong tournaments in the finished attic playroom, and making holiday ornaments at the large dining room table. There were also spaces to have quiet moments when you needed it...and we even enjoyed a beautiful hike at a nearby conservation area that Laurie recommended. The house was extremely clean, fully...
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
★PRIVATE 1 BDRM Newly Renovated Apt W/D Patio★
9.2 out of 10, Wonderful, 5 reviews
"Very clean, no bar soap for shower or instant creamer for coffee but excellent place."
The price is €199
per night
5 Jun - 6 Jun
★PRIVATE 1 BDRM Newly Renovated Apt W/D Patio★
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, 12 reviews
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, 66 reviews
"Probably one of the cleanest places I have ever stayed. The house is perfect. Beautiful views!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, 10 reviews
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, 4 reviews
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, 15 reviews
"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....
The Kemble- Built by a US Secretary of State in Lenox
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, 3 reviews
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, 2 reviews
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The Winthrop Estate - 12K SF 32 Acres
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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.

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The price is €111
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Hilton Albany
3.5 star property
7.0 out of 10, Good, 1,014 reviews
"The staff were very helpful and friendly! "
The price is €141
per night
16 Jun - 17 Jun
Hilton Albany
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.

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 €160 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?

Home away from home: This holiday home rental outside of Stephentown offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Stephentown?

Choose from 8 Expedia holiday rentals in Stephentown for a memorable holiday.

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 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.

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