Stockbridge Vacation Rentals from CA $165: Short-Term Rentals for 2026

Q: What are some of the best vacation rentals in Stockbridge?

Historic Stockbridge Villa on 25 acres : Visitors like this Stockbridge vacation home rental. It is located on a lake and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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Our top choices for Stockbridge vacation rentals

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

1. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveller

CA $1,182 total

includes taxes & fees

Sep 28 - Sep 29

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Pittsfield

Robert

CA $175 total

includes taxes & fees

Aug 31 - Sep 1

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

3. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

bob i.

CA $229 total

includes taxes & fees

Sep 7 - Sep 8

A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

4. stylish Berkshires Retreat

Lee

CA $561 total

includes taxes & fees

Sep 8 - Sep 9

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

5. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

CA $436 total

includes taxes & fees

Sep 8 - Sep 9

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

6. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

CA $443 total

includes taxes & fees

Sep 1 - Sep 2

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

7. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

CA $288 total

includes taxes & fees

Aug 31 - Sep 1

A wooden cabin with a covered deck, a fire pit, and string lights.

8. Huttopia Berkshires

Williamstown

GEORGINA

CA $151 total

includes taxes & fees

Sep 8 - Sep 9

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Top Stockbridge Hotel Reviews

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

Berkshire Mountain Lodge

8/10 Good

"the good….full kitchen, living room, king bedroom, clean bathroom, VERY reasonable nightly rate, especially for central berkshire county in the summer. there is no daily room cleaning, but extra towels, etc are always available from the front desk… the less than good…we’ve stayed here now u time in the past 18 months, but the last couple of stays the rooms have been a little musty and damp, despite (or because of?) the a/c being on constantly. ya gotta hold the handle down on the toilet to get a complete flush. no food service, but the is a stop&shop literally across the street… i would still recommend BML for the room rate and location alone…"

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"

Find out more about Stockbridge

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Stockbridge. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Stockbridge?

Yes, we offer vacation rentals in Stockbridge close to Berkshire Botanical Garden, or you can select a more secluded option if you want a relaxing stay. Our travelers 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 vacation rentals in Stockbridge?

Historic Stockbridge Villa on 25 acres: Visitors like this Stockbridge vacation home rental. It is located on a lake and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Stockbridge?

Choose from 35 Expedia vacation rentals in Stockbridge for a memorable vacation.

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 Schantz Galleries. National Shrine of the Divine Mercy and Stockbridge Bowl are other places to visit while you're in town.

What’s a vacation rental in Stockbridge like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Stockbridge. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips.

Stockbridge Vacation Rentals

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Check prices for these dates

Our top choices for Stockbridge vacation rentals

1. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

2. Berkshire Mountain Lodge

3. Cozy 1-bedroom studio in serene Great Barrington with AC

4. stylish Berkshires Retreat

5. Cozy Riverside Berkshires Retreat

6. Sweet Cozy Victorian in Housatonic. Close to everything.

7. NEW RENO - Chalet-style farm loft near Tanglewood

8. Huttopia Berkshires

9. Vacation Village in the Berkshires

10. Home in Great Barrington

11. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

12. The Brooks Motel: Exceptional Suite

13. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

14. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

15. 1800s Carriage house in Berkshires / Hudson Valley

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

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

18. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

19. Real Estate: Therapy - Lake, Laundry, Love it

20. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

Berkshires Untold

Find out more about Stockbridge

Explore a world of travel with Expedia

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