Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Holiday Rentals in Stockbridge

Our top choices for Stockbridge holiday rentals

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2020)
"All around loved everything about the place! "
The price is HK$808
HK$988 total
includes taxes & fees
5 Oct - 6 Oct
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (979)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"
The price is HK$1,159
HK$1,295 total
includes taxes & fees
19 Oct - 20 Oct
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is HK$762
HK$851 total
includes taxes & fees
29 Sept - 30 Sept
Huttopia Berkshires
The Ponds at Foxhollow
Indoor pool, outdoor pool, pool umbrellas, pool loungers

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (130)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is HK$1,252
HK$3,682 total
includes taxes & fees
28 Sept - 29 Sept
Comfortable Berkshires retreat on mtn resort, SISO
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is HK$2,274
HK$4,773 total
includes taxes & fees
1 Oct - 2 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is HK$4,658
HK$8,639 total
includes taxes & fees
29 Sept - 30 Sept
Hancock Village Inn at Jiminy Peak
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (223)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Outdoor banquet area

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (91)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (222)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake
The Lakeshore House
Property grounds

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is HK$3,771
HK$6,235 total
includes taxes & fees
26 Sept - 27 Sept
The Lakeshore House
Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is HK$2,869
HK$5,402 total
includes taxes & fees
29 Sept - 30 Sept
Guesthouse Cabin vacation rentals in Berkshire County
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (19)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Private Island - Largest Fresh Water Reservoir in Mass
Interior

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (65)
"Great value, so much better than all the touristy motels in the area!"
The price is HK$1,050
HK$1,614 total
includes taxes & fees
26 Sept - 27 Sept
Cozy Rustic Apt in 18th c Berkshire Farmhouse
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

8.0 out of 10, Very good, (8)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
The price is HK$1,136
HK$2,641 total
includes taxes & fees
22 Oct - 23 Oct
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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, (147)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (89)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
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

Hotel On North

Hotel On North

10/10 Excellent
"Great property! Very large clean room in a unique hotel! "
michelle 2-night trip
Posted 2 days ago
Hotel On North

Find out more about Stockbridge

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Stockbridge offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly.

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.