Stephentown Vacation Rentals

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Nov 13 - Nov 14
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Vacation Rentals in Stephentown

Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Our stay exceeded our expectations! The property is beautiful with a cute patio and modern furnishings/appliances. It had a homey and clean vibe and Dillon was nice enough to provide snacks, oatmeal, coffee, creamer, toothbrushes, etc. Everything we could need! We brought our two dogs and they seemed right at home and love going on walks through the fall leaves. Would definitely recommend for those with dogs, small children, or just traveling on their own!"
United States
Anja H.
$213 nightly
The price is $227
Nov 16 - Nov 17
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
$264 nightly
The price is $293
Nov 16 - Nov 17
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers
Fridge, microwave, oven, stovetop
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Stephentown
8.4 out of 10, Very Good, (12)
"The apartment is cozy, clean, and perfect for visiting Jiminy Peak."
United States
William G.
$244 nightly
The price is $260
Nov 20 - Nov 21
Total with taxes and fees
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$320 nightly
The price is $361
Nov 18 - Nov 19
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (6)
"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."
United States
Melissa D.
$320 nightly
The price is $361
Nov 17 - Nov 18
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (9)
"From the moment we walked in, the HunnyHaus felt like home—only better! Every detail was thoughtfully provided, from the fully stocked kitchen to cozy touches that made our stay so comfortable and relaxing. My husband and I kept saying throughout our trip that this was the perfect vacation. We were in the area for the John Williams Film Concert at Tanglewood performed by the Boston Pops, and the location was ideal. The hosts were incredible—friendly, responsive, and always ready with fantastic...
United States
Corey A.
$377 nightly
The price is $425
Nov 16 - Nov 17
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2133)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
$119 nightly
The price is $133
Nov 14 - Nov 15
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
$149 nightly
The price is $166
Nov 14 - Nov 15
Total with taxes and fees
Jiminy Peak Mountain Resort
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
$121 nightly
The price is $136
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
$166 nightly
The price is $184
Nov 14 - Nov 15
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford
10.0 out of 10, Exceptional, (27)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
$128 nightly
The price is $144
Nov 16 - Nov 17
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
WiFi, bed sheets
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Very cute! Perfect place for a weekend in the Berkshires"
United States
Melissa P.
$188 nightly
The price is $206
Nov 16 - Nov 17
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock
10.0 out of 10, Exceptional, (8)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
United States
Kevin K.
$211 nightly
The price is $236
Nov 17 - Nov 18
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock
10.0 out of 10, Exceptional, (4)
"This is my favorite unit of all the units I have stayed in! The pirate stuff was so cool and we could see our kids ski from the inside! The owner is so easy to communicate with. We love having the ability to cook and spread out while we are in the unit. We aaaaargh definitely going to stay here again!"
United States
Stephanie K.
$211 nightly
The price is $236
Nov 17 - Nov 18
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Fridge, microwave, oven, stovetop
The Bluebirds Nest

The Bluebirds Nest

Washington Square
7.4 out of 10, Good, (8)
"We were unimpressed with our stay at The Bluebird’s Nest. Outside of quick responsiveness for WiFi details, the experience wasn’t good. The apartment felt lived in with food in the refrigerator and dirty dishes in the dishwasher. There was garbage piled up under the stairs to the front door, electrical boxes with exposed wires and cracks around the tub. The beds and bedding were very uncomfortable (hard, hot and noisy). We would not stay again."
United States
Tim W.
$111 nightly
The price is $120
Dec 5 - Dec 6
Total with taxes and fees
The Bluebirds Nest
Dining tables
2 bed room Apartment

2 bed room Apartment

South End
10.0 out of 10, Exceptional, (4)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
$165 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
2 bed room Apartment
Fridge, microwave, oven, stovetop
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Bennington
8.6 out of 10, Excellent, (34)
"We had a lovely stay. The brook on the property is beautiful and peaceful. It was close to town but felt miles away."
United States
Sarah P.
$256 nightly
The price is $272
Nov 16 - Nov 17
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
TV
Florida Mountain Log Cabin

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"We loved our 1 night stay here - it is a super cute log cabin with comfortable beds and very clean! Our favorite part was the fire pit for smores and the kids especially loved the cozy swings! Host was very accessible. Definitely recommend!"
United States
Kate R.
$316 nightly
The price is $339
Nov 16 - Nov 17
Total with taxes and fees
Florida Mountain Log Cabin
Outdoor dining
2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water

Williamstown
9.4 out of 10, Exceptional, (10)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
$240 nightly
The price is $270
Nov 20 - Nov 21
Total with taxes and fees
2-Bdr Apt In Town, By the Water
Fridge, microwave, oven, stovetop
Business Travelers Retreat

Business Travelers Retreat

Albany
10.0 out of 10, Exceptional, (1)
"Place was as advertised and Rodney was a great host. Very responsive. Location was ideal for the Capital Region and parking was super convenient. Highly reccomend."
United States
Chas K.
$175 nightly
The price is $189
Nov 16 - Nov 17
Total with taxes and fees
Business Travelers Retreat
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere."
Kim 2-night trip
Posted 2 days ago
Berkshires Untold

Find out more about Stephentown

Everything you need to know about Stephentown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stephentown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stephentown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Stephentown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $120 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stephentown rentals

At Expedia, we put the best Stephentown vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This vacation home near Stephentown offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a fridge, a stovetop, and a coffee maker, so you can cook with friends or family. You can relax into your vacation with a garden and foosball.

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 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.