Stephentown Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday 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.
The price is HK$832
HK$1,765 total
includes taxes & fees
13 Nov - 14 Nov
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.
The price is HK$1,205
HK$2,485 total
includes taxes & fees
17 Nov - 18 Nov
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.
The price is HK$1,020
HK$2,023 total
includes taxes & fees
20 Nov - 21 Nov
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.
The price is HK$1,671
HK$2,805 total
includes taxes & fees
18 Nov - 19 Nov
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.
The price is HK$1,671
HK$2,804 total
includes taxes & fees
17 Nov - 18 Nov
BLUSH: Boutique TINY home*private spa*walk to town
Smart TV, fireplace
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.
The price is HK$1,827
HK$3,305 total
includes taxes & fees
16 Nov - 17 Nov
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
The price is HK$764
HK$938 total
includes taxes & fees
14 Nov - 15 Nov
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
The price is HK$1,124
HK$1,255 total
includes taxes & fees
13 Nov - 14 Nov
Jiminy Peak Mountain Resort
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
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.
The price is HK$971
HK$1,423 total
includes taxes & fees
18 Nov - 19 Nov
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.
The price is HK$532
HK$1,118 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is HK$1,049
HK$1,614 total
includes taxes & fees
13 Nov - 14 Nov
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.
The price is HK$816
HK$1,832 total
includes taxes & fees
17 Nov - 18 Nov
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.
The price is HK$816
HK$1,832 total
includes taxes & fees
17 Nov - 18 Nov
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.
The price is HK$482
HK$982 total
includes taxes & fees
5 Dec - 6 Dec
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.
The price is HK$738
HK$1,385 total
includes taxes & fees
13 Nov - 14 Nov
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.
The price is HK$777
HK$2,095 total
includes taxes & fees
13 Nov - 14 Nov
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.
The price is HK$1,428
HK$2,635 total
includes taxes & fees
13 Nov - 14 Nov
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.
The price is HK$933
HK$2,097 total
includes taxes & fees
20 Nov - 21 Nov
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.
The price is HK$630
HK$1,435 total
includes taxes & fees
13 Nov - 14 Nov
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
Stacey 2-night trip
Posted 4 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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:

  • View our selection of featured holiday rentals in Stephentown
  • Use the map to find apartments and other holiday homes in the Stephentown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Stephentown while they last

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

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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This holiday home rental outside of Stephentown offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and table football.

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.