Stockbridge Holiday Rentals from AU$166: Search Short-Term Rentals

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

Historic Stockbridge Villa on 25 acres : This highly rated holiday home rental in Stockbridge is located on a lake, and has an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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In two weeks

In two months

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In four months

Our top choices for Stockbridge holiday 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

includes taxes & fees

28 Sept - 29 Sept

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

2. Berkshire Mountain Lodge

Pittsfield

Robert

includes taxes & fees

31 Aug - 1 Sept

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.

includes taxes & fees

7 Sept - 8 Sept

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

includes taxes & fees

8 Sept - 9 Sept

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.

includes taxes & fees

8 Sept - 9 Sept

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.

includes taxes & fees

1 Sept - 2 Sept

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.

includes taxes & fees

31 Aug - 1 Sept

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

8. Huttopia Berkshires

Williamstown

GEORGINA

includes taxes & fees

8 Sept - 9 Sept

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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!"

Find out more about Stockbridge

Everything you need to know about Stockbridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Stockbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge holiday rentals we have selected for you start as low as AU$166 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Historic Stockbridge Villa on 25 acres: This highly rated holiday home rental in Stockbridge is located on a lake, and has an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Stockbridge?

Choose from 35 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 Schantz Galleries. National Shrine of the Divine Mercy and Stockbridge Bowl 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.

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Check prices for these dates

Our top choices for Stockbridge holiday 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 holiday rentals that suit your style

Top Stockbridge Hotel Reviews

Berkshires Untold

The Yankee Inn

Vacation Village in the Berkshires

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

The Red Lion Inn

Find out more about Stockbridge

Frequently asked questions

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