Great Barrington Vacation Rentals from CA $175: Short-Term Rentals for 2026

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

Cozy Riverside Berkshires Retreat : This highly rated vacation home rental in Great Barrington is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! as a favorite home for rent in Great Barrington.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Great Barrington vacation rentals

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

bob i.

CA $229 total

includes taxes & fees

Sep 7 - Sep 8

2. Home in Great Barrington

Great Barrington

HEATHER G.

CA $562 total

includes taxes & fees

Sep 3 - Sep 4

3. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

CA $436 total

includes taxes & fees

Sep 8 - Sep 9

Beach nearby, sun loungers, beach towels

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

Great Barrington

Kristin O.

CA $513 total

includes taxes & fees

Sep 14 - Sep 15

3 bedrooms, iron/ironing board, WiFi, bed sheets

5. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

CA $773 total

includes taxes & fees

Sep 8 - Sep 9

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

Great Barrington

Rebecca K.

CA $1,847 total

includes taxes & fees

Aug 31 - Sep 1

7. Berkshire Mountain Lodge

Pittsfield

Robert

CA $175 total

includes taxes & fees

Aug 31 - Sep 1

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

Housatonic

Peter S.

CA $443 total

includes taxes & fees

Sep 1 - Sep 2

Desk, iron/ironing board, WiFi, bed sheets

9. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

CA $265 total

includes taxes & fees

Aug 31 - Sep 1

10. Micosta Leisure Inn

Hudson

Andrea

CA $211 total

includes taxes & fees

Sep 1 - Sep 2

11. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

CA $719 total

includes taxes & fees

Sep 22 - Sep 23

12. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

CA $807 total

includes taxes & fees

Sep 21 - Sep 22

13. stylish Berkshires Retreat

Lee

CA $561 total

includes taxes & fees

Sep 8 - Sep 9

14. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Hillsdale

CA $942 total

includes taxes & fees

Aug 31 - Sep 1

15. 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

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

Sherwood Forest

Sharon K.

CA $520 total

includes taxes & fees

Sep 9 - Sep 10

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

Sherwood Forest

Frank M.

CA $547 total

includes taxes & fees

Sep 7 - Sep 8

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

Dalton

Megan A.

CA $451 total

includes taxes & fees

Aug 31 - Sep 1

19. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted

Steve

CA $329 total

includes taxes & fees

Sep 1 - Sep 2

4 bedrooms, travel crib, WiFi, bed sheets

20. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

CA $1,214 total

includes taxes & fees

Sep 2 - Sep 3

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Top Great Barrington Hotel Reviews

Pocketbook Hotel and Bath

10/10 Excellent

"It was an amazing one night stay for us! Clean rooms, attentive staff, and the Baths were amazing."

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 Great Barrington

Everything you need to know about Great Barrington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Barrington vacation rental for you. At Expedia, you can take your pick from private vacation 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 Great Barrington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Barrington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Barrington. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Barrington vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Barrington vacation rentals we have selected for you start as low as CA $175 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Great Barrington rentals

At Expedia, we put the best Great Barrington vacation 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 Great Barrington 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 Great Barrington vacation.

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

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Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals in Great Barrington close to Mahaiwe Performing Arts Center, or you can select a more secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theater scene during your trip.

What are some of the best vacation rentals in Great Barrington?

Cozy Riverside Berkshires Retreat: This highly rated vacation home rental in Great Barrington is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! as a favorite home for rent in Great Barrington.

How many vacation rentals are there in Great Barrington?

With 94 Expedia vacation rentals, you're sure to find just the right place for your Great Barrington stay.

What can I see and do in Great Barrington?

Housatonic River Walk and Housatonic River are a couple of scenic spots to enjoy the outdoors, whereas Art et Industrie is one of the cultural attractions. Mahaiwe Performing Arts Center and Lake Mansfield Park are other places to visit while you're in town.

What are vacation rentals like in Great Barrington?

Vacation rentals are privately owned properties you can reserve for several days or more in Great Barrington. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion 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 hotel, which makes a vacation rental a great choice for a family getaway.

Great Barrington Vacation Rentals

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Check prices for these dates

Our top choices for Great Barrington vacation rentals

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

2. Home in Great Barrington

3. Cozy Riverside Berkshires Retreat

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

5. Cozy. Clean. Free bagel shop. 3 Fireplaces.

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

7. Berkshire Mountain Lodge

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

9. The Brooks Motel: Exceptional Suite

10. Micosta Leisure Inn

11. Cheerful 3-bedroom cottage with woodstove

12. Treetop Hideaway in Tyringham

13. stylish Berkshires Retreat

14. Fantastic 2-bedroom house with AC in quaint Hillsdale.

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

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

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

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

19. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

20. Stylish Mid-century Modern Berkshires Cape

Find vacation rentals that suit your style

Top Great Barrington Hotel Reviews

Pocketbook Hotel and Bath

Find out more about Great Barrington

Explore a world of travel with Expedia

Frequently asked questions

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