Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Stockbridge

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2136)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is HK$784
HK$961 total
includes taxes & fees
18 Nov - 19 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, (985)
"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$1,123
HK$1,255 total
includes taxes & fees
18 Nov - 19 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, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Fridge, microwave, oven, stovetop
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
18 Nov - 19 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
Huttopia Berkshires

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,469
HK$1,641 total
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
10.0 out of 10, Exceptional, (9)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
United States
Robert B.
The price is HK$3,187
HK$5,557 total
includes taxes & fees
18 Nov - 19 Nov
Guesthouse Cabin vacation rentals in Berkshire County
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is HK$1,245
HK$3,049 total
includes taxes & fees
18 Nov - 19 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
The price is HK$1,133
HK$2,933 total
includes taxes & fees
19 Nov - 20 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is HK$816
HK$1,832 total
includes taxes & fees
18 Nov - 19 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is HK$1,049
HK$1,884 total
includes taxes & fees
18 Nov - 19 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,421
HK$10,357 total
includes taxes & fees
18 Nov - 19 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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
18 Nov - 19 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
1 bedroom, iron/ironing board, WiFi, bed sheets
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Hancock
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
The price is HK$816
HK$1,832 total
includes taxes & fees
18 Nov - 19 Nov
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$3,304
HK$6,147 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is HK$1,003
HK$2,700 total
includes taxes & fees
18 Nov - 19 Nov
UNIQUE - 1BR Country Condo @ Jiminy Peak
Indoor pool
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock
10.0 out of 10, Exceptional, (3)
"Great spot. Great communication. Comfortable suite."
United States
Samuel
The price is HK$816
HK$1,832 total
includes taxes & fees
18 Nov - 19 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
The price is HK$1,224
HK$2,062 total
includes taxes & fees
18 Nov - 19 Nov
Home in Great Barrington
Exterior
Bungalow in the Berkshires

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
The price is HK$2,138
HK$2,996 total
includes taxes & fees
30 Nov - 1 Dec
Bungalow in the Berkshires
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$749
HK$1,668 total
includes taxes & fees
23 Nov - 24 Nov
Berkshires Apartment at the Stephentown Hotel
Exterior
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
The price is HK$816
HK$1,832 total
includes taxes & fees
18 Nov - 19 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
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 Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great stay!"
Ann 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Stockbridge

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

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

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

Frequently asked questions

Can I find a holiday rental in Stockbridge?

Yes, there are holiday rentals in Stockbridge close to Berkshire Botanical Garden, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Stockbridge has a good selection of bars. Make sure you have time to check out the gardens and museums during your trip.

What are some of the best holiday rentals that Stockbridge has to offer?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Stockbridge is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Stockbridge?

Choose from 30 Expedia holiday rentals in Stockbridge for a memorable holiday.

What’s there to see and do in Stockbridge?

Enjoy the outdoors at Naumkeag Museum and Berkshire Botanical Garden, or simply take in cultural attractions like Norman Rockwell Museum and Frelinghuysen Morris House and Studio. National Shrine of the Divine Mercy and Housatonic River are other places to visit while you're in town.

What’s a holiday rental in Stockbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stockbridge. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.