Great Barrington Vacation Rentals from CA $206: Short-Term Rentals for 2026

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

Cozy Riverside Berkshires Retreat : Visitors give good reviews to this Great Barrington vacation home rental, which 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 an electric kettle, 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.

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Our top choices for Great Barrington vacation rentals

Micosta Leisure Inn

Hudson

Kathleen

CA $206 total

includes taxes & fees

Jun 30 - Jul 1

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

CA $784 total

includes taxes & fees

Jun 30 - Jul 1

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Top Great Barrington Hotel Reviews

The Yankee Inn

10/10 Excellent

"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."

The Red Lion Inn

8/10 Good

"I did not stay in the main building but had a room in a separate building on the same block. I quite liked my room away from the inn. It was roomy, quiet, across the street from a church, easy walk to the cafe, and there was a bunny 🐰 eating grass outside each night. I think I will request such a room away from the hubbub when I return. The food at the Red Lion's Inn's 'Widow's' tavern was delicious. Just know the buildings are indeed OLD so if you are seeking great water pressure or modern vibe, this is not your place. Love the history of this place!"

East Rock Inn

10/10 Excellent

"The entire property has been relatively recently renovated, and it shows. Our room was in excellent condition, everything worked. Super clean, and everything in the bathroom was new and fully working. The bed was unusually comfortable. The property was quiet overnight (on a weekend) so we slept very well. Air conditioning was fully satisfactory. Although the property is "automated" in the sense that there is no front desk to speak of, and you use a 4-digit code to enter your room and access the ice machine, there was plenty of communication from the management (by text message) so I felt sufficiently "in contact" with them. Just be aware that the rooms are on the small side. Perfectly adequate and a very good value for the price, but let's just say you'll need to think through where you'll be putting all your belongings. We had packed light for a one-night stay, so it was all good. I don't think there was any breakfast available, but we didn't check - we had somewhere to be for breakfast on our check-out day. There aren't any dining options within walking distance, but it's only 1-2 miles into town where there are plenty of options. Overall we would definitely stay again. This area is quite pricey during Tanglewood season, so the East Rock Inn offers a clean, quiet, safe, well-maintained place to stay at a very good value."

Quality Inn Great Barrington

8/10 Good

"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain time for a gathering."

Berkshire Mountain Lodge

10/10 Excellent

"Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful staff, great price for a great room( separate dining area, living area, bedroom and huge bathroom!!!!!) extra clean woukd def go back"

Find out more about Great Barrington

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 Great Barrington. 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 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: Visitors give good reviews to this Great Barrington vacation home rental, which 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 an electric kettle, 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.

How many vacation rentals are there in Great Barrington?

With 106 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.

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Check prices for these dates

Our top choices for Great Barrington vacation rentals

Micosta Leisure Inn

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Find vacation rentals that suit your style

Top Great Barrington Hotel Reviews

The Yankee Inn

The Berkshire Mountain Inn

The Red Lion Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

East Rock Inn

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

Quality Inn Great Barrington

Berkshire Mountain Lodge

Find out more about Great Barrington

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