Great Barrington Holiday Rentals from AU$160: Search Short-Term Rentals

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

Riverside Retreat in the Berkshires : This highly rated holiday home rental in Great Barrington is located on a river, and has a fireplace, a selection of games 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 that you can cook with friends or family. Some other top choices in Great Barrington are Great Barrington, Cabin Sleeps 14, Walk To Town and Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! .

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Great Barrington holiday rentals

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

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

Great Barrington

Deborah S.

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

2. Home in Great Barrington

Great Barrington

Janet G.

includes taxes & fees

26 Oct - 27 Oct

A sandy beach with a lake and forest in the background.

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

Great Barrington

Kristin O.

includes taxes & fees

16 Nov - 17 Nov

A staircase with a wooden handrail and a white wall with a light switch.

4. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Great Barrington

Mark M.

includes taxes & fees

17 Nov - 18 Nov

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

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

Great Barrington

Roberta

includes taxes & fees

22 Oct - 23 Oct

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

7. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Great Barrington

includes taxes & fees

23 Oct - 24 Oct

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

8. Berkshire Mountain Lodge

Pittsfield

Joel

includes taxes & fees

10 Nov - 11 Nov

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

9. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

29 Oct - 30 Oct

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

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

Housatonic

Peter S.

includes taxes & fees

22 Oct - 23 Oct

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

11. Micosta Leisure Inn

Hudson

George

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

12. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

3 Nov - 4 Nov

A wooden deck with a staircase leading to a covered porch area.

13. All comforts of home

Hudson

Douglas

includes taxes & fees

27 Oct - 28 Oct

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

14. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

includes taxes & fees

21 Oct - 22 Oct

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

includes taxes & fees

3 Nov - 4 Nov

A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

16. Mayas Shangrila

Richmond

includes taxes & fees

25 Oct - 26 Oct

A wooden cabin with a porch, a grill, and a flower planter.

17. Ideal location for summer and winter activities with plenty of outdoor space.

Hillsdale

Richard M.

includes taxes & fees

23 Oct - 24 Oct

18. All the comforts of home

Hudson

Lori M.

includes taxes & fees

26 Oct - 27 Oct

A serene lakeside view with a clear path leading to a small cabin, surrounded by dense trees and tall grasses.

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

Sherwood Forest

Sharon K.

includes taxes & fees

3 Nov - 4 Nov

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

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

New Lebanon

Joanna P.

includes taxes & fees

18 Nov - 19 Nov

View all properties

Find holiday rentals that suit your style

Private holiday homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Great Barrington Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The unit was clean and comfortable. Location was nice and quiet. Mini golf and hot tub were fun and appreciated. Unit was dated- cabinets were old. Kitchen was well- stocked. I would suggest having kitchen towels though. Blankets would have been nice ( as the weather was changing.)."

Berkshires Untold

8/10 Good

"We were surprised when we arrived to find that the hotel was actually a converted motel. The website doesn’t show any pictures to indicate this which is a bit of false advertising. But we were able to look past that because the lobby/restaurant area was very cute and cozy. Nice breakfast options and free coffee and tea (but they only offered 1 variety of tea). Rooms were pretty standard, bathroom was bigger than I anticipated. Loved the Le Labo products- nice touch. Rooms were clean, but we realized that housekeeping never came the 3 nights we were there. Not sure if we were supposed to request it each day, but it was kinda strange that they never even came to clear out the garbage cans. The outdoor patio was nice but it was a bit too cold for us to use even though they did have fire pits. Not sure I would go back. If was also on a main road so you could hear the cars & trucks. I’d probably look for better options in the area before I settled on this again."

The Little Lion

10/10 Excellent

"Quaint location that is loosely tied to the Historic Red Lion Inn at Stockbridge. There is no on site staff so everything is done through texting. You do get access to the Red Lion Inn which was a wonderful "amenity" without the cost of staying there. The Little Lion is a roadside motel with about 14 or 15 units. Very clean and obviously quiet. Was a great home base for a couple of days while we tooled around the Berkshires. Would definitely book again!"

Cozy 1-bedroom studio in serene Great Barrington with AC

10/10 Excellent

"Location was perfect for exploring Great Barrington as well as it’s proximity to Stockbridge. Although the room was compact, it was more than adequate for my needs. The room itself is extremely clean and the laying out of towels with small soaps and chocolates and it seemed like a five star hotel - excellent touch.The room had a full kitchen, full-size refrigerator. The drip coffee maker along with the Keurig will be appreciated by coffee lovers. I especially liked the fact that there were dark roast coffee K cups on hand. Walk to downtown Great Barrington was only a few minutes and there are plenty of shops and places to grab a coffee or tea as well as several bars and restaurants. The people are friendly and a young couple I met suggested I visit the Barrington brewery, just a few miles north on Route 7. The brewery has a full kitchen. a good menu, and good quality food, whether it be small plates, entrées, or sandwiches. They make their own desserts.When my future plans bring me to the area again, I will definitely stay at this location. The owner was more than accommodating and is quite considerate. Five stars from me."

Find out more about Great Barrington

Everything you need to know about Great Barrington 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 Great Barrington 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 Great Barrington holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Great Barrington holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Barrington 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 Great Barrington holiday rentals we have selected for you start as low as AU$160 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Great Barrington rentals

At Expedia, we put the best Great Barrington 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 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 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 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.

Frequently asked questions

Can I find a holiday rental in Great Barrington?

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

What are some of the best holiday rentals that Great Barrington has to offer?

Riverside Retreat in the Berkshires: This highly rated holiday home rental in Great Barrington is located on a river, and has a fireplace, a selection of games 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 that you can cook with friends or family. Some other top choices in Great Barrington are Great Barrington, Cabin Sleeps 14, Walk To Town and Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!.

How many holiday rentals are there in Great Barrington?

With 96 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Great Barrington?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Great Barrington. Holiday rentals offer amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Great Barrington holiday rentals

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

2. Home in Great Barrington

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

4. Leaf-Peeper Paradise in the Berkshires

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

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

7. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

8. Berkshire Mountain Lodge

9. The Brooks Motel: Exceptional Suite

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

11. Micosta Leisure Inn

12. Cheerful 3-bedroom cottage with woodstove

13. All comforts of home

14. Secluded Family Home in Serene Stockbridge Woods

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

16. Mayas Shangrila

17. Ideal location for summer and winter activities with plenty of outdoor space.

18. All the comforts of home

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

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

Find holiday rentals that suit your style

Top Great Barrington Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Berkshire Mountain Lodge

Monument Mountain Motel

Berkshires Untold

Quality Inn Great Barrington

Pocketbook Hotel and Bath

The Little Lion

East Rock Inn

Cozy 1-bedroom studio in serene Great Barrington with AC

Find out more about Great Barrington

Frequently asked questions

Go further with the Expedia app