Stockbridge Holiday Rentals

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Holiday Rentals in Stockbridge

Tranquil Retreat 6-BRs Total in the Berkshires

The price is NZ$2,624
includes taxes & fees
7 July - 8 July
Tranquil Retreat 6-BRs Total in the Berkshires

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is NZ$617
includes taxes & fees
25 June - 26 June
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is NZ$259
includes taxes & fees
29 June - 30 June
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is NZ$1,438
includes taxes & fees
1 July - 2 July
Spacious 5-bedroom house in charming Lee with WiFi

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is NZ$629
includes taxes & fees
25 June - 26 June
Home in Great Barrington

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is NZ$933
includes taxes & fees
25 June - 26 June
Great Barrington Get Away

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (69)
"We had a wonderful stay, thank you! "
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is NZ$800
includes taxes & fees
25 June - 26 June
Comfortable Berkshires retreat on mtn resort, SISO

Serene 5-BR Retreat 9-Min to Catamount

2.0 star property
10.0 out of 10, Exceptional, (4)
"Highly recommended. The how is beautiful, the pool is a great feature. We will book again"
The price is NZ$2,984
includes taxes & fees
23 July - 24 July
Serene 5-BR Retreat 9-Min to Catamount

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is NZ$1,837
includes taxes & fees
8 July - 9 July
Hancock Village Inn at Jiminy Peak

Enchanting Cottage, Come Enjoy Nature!

10.0 out of 10, Exceptional, (1)
"If you want TV, this isnt for you, but if you want a quiet place to check away and relax it fits the bill wonderfully"
The price is NZ$1,724
includes taxes & fees
5 July - 6 July
Enchanting Cottage, Come Enjoy Nature!

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is NZ$783
includes taxes & fees
30 June - 1 July
NEW RENO Historic Creamery in Berkshires w/hot tub

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is NZ$997
includes taxes & fees
6 July - 7 July
Perfect House In Hillsdale, Brings Friends & Fam

Majestic views Hot tub Firepit Games Sleeps 14

The price is NZ$3,009
includes taxes & fees
18 July - 19 July
Majestic views Hot tub Firepit Games Sleeps 14

Wolf Hill Acres: A Charming & Modern Country Home

10.0 out of 10, Exceptional, (1)
"7 of us, 60 year old friends plus young adult had a fabulous time over 4 days including NY’s eve, cooking together, playing pool,ping pong, watching movies, taking walks from house, a little time in Great Barrington, Hudson and Kingston! Great beds! We’re eager to come back iin summer!!"
The price is NZ$2,115
includes taxes & fees
13 July - 14 July
Wolf Hill Acres: A Charming & Modern Country Home

The Lakeshore House

The price is NZ$1,279
includes taxes & fees
7 July - 8 July
The Lakeshore House
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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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?

Deluxe Queen Room with 2 Queen Beds: This holiday home rental outside of Stockbridge is equipped with an outdoor pool, air conditioning and WiFi to help you feel comfortable during your stay.

How many holiday rentals will I find in Stockbridge?

Choose from 27 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 Mission House. 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.