Great Barrington Holiday Rentals, Massachusetts: Private House Rentals

A large stone church with a tall bell tower and arched windows.

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Go beyond your typical stay in Great Barrington

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Our top choices for Great Barrington hotels

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

3.718.380 ₫

4.153.430 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A breakfast area with a counter, coffee machine, and a display of pastries.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Cynthia

2.148.455 ₫

2.399.824 ₫ total

includes taxes & fees

17 Nov - 18 Nov

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A Quality Inn sign, a brick building, and a parking lot with cars.

3. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

1.958.200 ₫

2.187.309 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden wall with a white pendant light fixture.

4. Prospect Berkshires

Egremont

Conor

7.338.397 ₫

9.064.396 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A large house with a balcony and a grassy yard.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

5. The Little Lion

Great Barrington

Lidia

2.679.097 ₫

2.992.552 ₫ total

includes taxes & fees

20 Oct - 21 Oct

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

6. Monument Mountain Motel

Great Barrington

Andrea

1.549.217 ₫

1.730.412 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

7. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Ramakrishnan

2.044.915 ₫

2.284.170 ₫ total

includes taxes & fees

20 Oct - 21 Oct

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

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

8. East Rock Inn

Great Barrington

Sharon

3.257.317 ₫

3.638.423 ₫ total

includes taxes & fees

19 Nov - 20 Nov

A dining area with round tables set for two, a fireplace, and a mural on the wall.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

A white two-story house with a front door, windows, and a chimney.

9. The Old Inn On The Green

Great Barrington

John

7.506.650 ₫

9.058.197 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A bar with wooden floors and shelves filled with bottles.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A covered porch with wicker furniture and hanging flower baskets.

10. The Red Lion Inn

Stockbridge

Stephan

4.077.405 ₫

5.840.428 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A house with a stone patio and wooden stools.

11. Little Cat Lodge

Copake Falls

Stacy

3.937.108 ₫

4.409.560 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

12. Quality Inn Lee - Lenox South

Lee

Lucinda

2.398.245 ₫

2.678.839 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

13. Granville House

Housatonic

Cynthia

6.574.790 ₫

7.344.092 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A building with a porch and multiple windows, surrounded by purple flowers.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

14. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

Michael

3.028.545 ₫

3.888.963 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

15. The Yankee Inn

Lenox

Basil

2.743.810 ₫

3.064.835 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A dining area with large windows, wooden furniture, and a view of a lake.

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside dock with kayaks and a covered boat ramp.

16. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Gustavo

2.948.302 ₫

3.293.254 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

17. Wilder House Berkshires

Sheffield

Mark

4.241.593 ₫

4.737.859 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

18. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

3.251.415 ₫

3.631.829 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a brick entrance and a white facade.

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

A neatly arranged bedroom with a bed, bedside table, and a dresser.

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

19. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Philippe

9.886.090 ₫

11.959.350 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A hotel room with a bed, a desk, and two wall-mounted lamps.

A motel with a flagpole, a blue awning, and a parking lot.

A small kitchenette with a coffee maker, toaster, and cabinets. There is a red and green patterned floor and a plant on the left.

A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.

20. Econo Lodge Lee - Great Barrington

Lee

Anna

1.694.173 ₫

1.892.391 ₫ total

includes taxes & fees

13 Nov - 14 Nov

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Where to stay in Great Barrington

Find the best Great Barrington areas for the activities you enjoy most.

Downtown Great Barrington

Downtown Great Barrington

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Stay near popular Great Barrington attractions

Lake Mansfield Park

9.0/10 (22 reviews)

This serene 29-acre lake offers swimming, boating, and fishing amid a conservation forest. Enjoy the sandy beach and shaded picnic areas, or explore wildlife along accessible walking trails through the adjacent woodland.

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Ski Butternut

9.0/10 (134 reviews)

Ski Butternut offers 22 diverse trails across 110 acres of terrain suitable for all skill levels. Morning visits reward skiers with freshly groomed slopes and the satisfaction of first tracks.

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Mahaiwe Performing Arts Center

9.0/10 (22 reviews)

This 1905 theatre offers an intimate setting with exceptional acoustics for music, dance, and film. Enjoy diverse performances in this beautifully restored historic venue known for its perfect sightlines.

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Housatonic River Walk

9.2/10 (76 reviews)

Restored from an industrial past, this riverside trail showcases the Housatonic's natural beauty and ecological rebirth. Stroll the free path with interpretive displays highlighting conservation efforts.

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Lake Buel

8.8/10 (23 reviews)

This serene Berkshire lake offers clear waters and picturesque surroundings for fishing and boating enthusiasts. Rent a kayak to explore hidden coves or enjoy the spectacular fall foliage reflecting on the water.

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Monument Mountain

This historic Berkshire peak inspired Melville and Hawthorne during their famous 1850 hike. Follow their literary footsteps to Devil's Pulpit for panoramic valley views framed by vibrant seasonal foliage.

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Jug End State Reservation

8.8/10 (3 reviews)

This Berkshire Mountains sanctuary offers a 2-mile loop through meadows and forests with panoramic valley views. Autumn visitors are rewarded with vibrant foliage displays along well-maintained, uncrowded trails.

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W.E.B. Du Bois Boyhood Homesite

8.8/10 (29 reviews)

Walk the interpretive trail where civil rights pioneer W.E.B. Du Bois spent his childhood. This National Historic Landmark offers a serene space to reflect on Du Bois's legacy through archaeological remains.

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Learn more about Great Barrington

Tucked in the Berkshires, this charming town blends historic Main Street shopping with easy access to Monument Mountain's panoramic hiking trails. Visit in autumn when the maple-lined streets burst with colour, or catch performances at the Mahaiwe Theatre housed in a beautifully restored 1905 building.

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A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

Top Great Barrington Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"I had a one BR suite for 4 nights and it was a perfect amount of space for 3 people. Kitchen was very well-equipped and convenient to have for making simple meals and reheating leftovers. While all the cooking utensils/ basics were provided, remember to bring all your oil/ spices as I did. I can't believe there was even a blender to use! Bedroom was spacious with comfortable bed. I can't say the same for the sofa bed, but that's expected. The entire space may appear slightly dated (doesn't bother me), but everything was clean and completely functional, which was allI wanted and needed. If you are a light sleeper, it may help to be in a corner room as walls might be somewhat thinner for some."

Quality Inn Great Barrington

10/10 Excellent

"-"

The Yankee Inn

8/10 Good

"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"G"

Pocketbook Hotel and Bath

8/10 Good

"Spa was lovely."

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent

"Good value for the price"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

8/10 Good

"Property grounds weren’t maintained well. Bathroom faucet was lose."

East Rock Inn

8/10 Good

"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."

Gedney Farm

10/10 Excellent

"Beautiful location with a fantastic chef and meal options. Lee the bartender was great, too!"

More cheap stays in Great Barrington