Glendale Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Glendale hotels

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

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

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

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

Great Barrington

Lisa

฿6,359

฿7,103 total

includes taxes & fees

30 Aug - 31 Aug

A Holiday Inn Express & Suites building with a stone facade, a covered entrance, and a parking lot.

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

A buffet with labeled containers for omelets and other dishes.

An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.

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

Great Barrington

BJORN

฿4,018

฿4,489 total

includes taxes & fees

23 Sept - 24 Sept

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

A covered porch with wicker furniture and hanging flower baskets.

A bar with wooden floors and shelves filled with bottles.

A backyard with a swimming pool, lounge chairs, and a hot tub.

3. The Red Lion Inn

Stockbridge

Patricia

฿5,146

฿7,371 total

includes taxes & fees

8 Sept - 9 Sept

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.

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

4. Quality Inn Lee - Lenox South

Lee

Christine

฿3,582

฿4,001 total

includes taxes & fees

14 Sept - 15 Sept

A red building with a sign reading "Shaker Mill Inn."

A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

5. Shaker Mill Inn

West Stockbridge

Mervin

฿5,848

฿6,415 total

includes taxes & fees

26 Aug - 27 Aug

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 two-story building with a gabled roof and a chimney.

6. The Little Lion

Great Barrington

Anne

฿3,675

฿4,105 total

includes taxes & fees

1 Sept - 2 Sept

A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

A kitchenette with a refrigerator, coffee maker, toaster, and bread display.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

A motel with multiple rooms, a well-maintained lawn, and a stone pathway.

7. Econo Lodge Lee - Great Barrington

Lee

Anna

฿2,323

฿2,595 total

includes taxes & fees

7 Sept - 8 Sept

A serene riverside view with a stone bridge, reflecting trees and buildings.

A multi-story hotel with balconies, a pond with rocks, and a clear sky.

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

A café with a display case, a frozen food section, and a marketplace sign.

8. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Claudia

฿3,822

฿4,908 total

includes taxes & fees

31 Aug - 1 Sept

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

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

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

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

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

Stockbridge

Philippe

฿10,787

฿13,049 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

Lee

James

฿4,165

฿4,653 total

includes taxes & fees

14 Sept - 15 Sept

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

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

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

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

11. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Elspeth

฿2,581

฿2,883 total

includes taxes & fees

1 Sept - 2 Sept

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

12. Brook Farm Inn

Lenox

Carrie

฿9,042

฿10,361 total

includes taxes & fees

30 Aug - 31 Aug

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.

A covered outdoor area with stone pillars and a view of a road and green hills.

13. Courtyard by Marriott Lenox Berkshires

Lenox

Laura

฿5,804

฿6,483 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

14. Quality Inn Great Barrington

Great Barrington

Sisile

฿3,027

฿3,381 total

includes taxes & fees

13 Sept - 14 Sept

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

15. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Jermaine

฿3,724

฿4,159 total

includes taxes & fees

1 Sept - 2 Sept

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

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

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

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

16. Granville House

Housatonic

Nicole

฿8,984

฿10,036 total

includes taxes & fees

26 Aug - 27 Aug

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

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

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.

17. Monument Mountain Motel

Great Barrington

John

฿2,793

฿3,120 total

includes taxes & fees

1 Sept - 2 Sept

A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

A living room with a fireplace, leather sofas, and a dog.

18. The Inn at Stockbridge

Stockbridge

Michele

฿12,316

฿14,445 total

includes taxes & fees

13 Sept - 14 Sept

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

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

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

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

19. The Yankee Inn

Lenox

Karen

฿5,162

฿5,766 total

includes taxes & fees

14 Sept - 15 Sept

A large, two-story house with a well-maintained lawn and a fence.

A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

20. Devonfield Inn B&B

Lee

Richard

฿12,709

฿14,195 total

includes taxes & fees

3 Sept - 4 Sept

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Top Glendale Hotel Reviews

Hotel On North

8/10 Good

"It’s a good place to stay. The rooms are but dark and could you add more lamps to the room?"

Quality Inn Lee - Lenox South

8/10 Good

"Clean room, surprisingly comfortable bed. Convenient, functional, for a short stay."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s pillow, a wonderful indoor and outdoor dance performance venue. We stay there often, and always makes four a cultural experience and wonderful family time."

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"It's an old property and it looks it with outdated interior and exterior, stains on really worn carpet, one light out in the room (we lived without it), tiny bathroom and towels so worn out they felt like sandpaper. However, the bed was exactly what I like: mattress was firm enough, bed linens were bright white, pillows were plump enough, and I slept decently. The blinds were truly light-blocking and they closed well. The reason we stayed here was to sleep overnight before heading home the next day, so that objective was achieved. Breakfast included bacon and buffet was stocked. Other breakfast guests were pleasant. Desk staff members did what they were supposed to do. There was a mini fridge, which I wanted so we could have cold drinks for the day we departed. As I recall from reserving two months ago, the rate was a good deal. Would not stay longer than one night, but for a single night, this was a problem-free experience."

Berkshires Untold

10/10 Excellent

"Great stay, friendly staff, met all of our needs."

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

10/10 Excellent

"Our entire stay was exemplary!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"I liked the balcony overlooking the lake"

The Whitlock

8/10 Good

"This is a very quaint hotel in a fantastic location. It is easy to walk to everything in Lenox and even Tanglewood from the hotel. Just be aware it is an uphill walk back from Tanglewood. The room was very spacious and bed very comfortable. Would definitely stay here again. If looking for any opportunities to improve, only thing I can come up with is a small frig in the room. Great place!"

The Yankee Inn

8/10 Good

"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."

More cheap stays in Glendale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,029

฿2,266 total

25 Aug - 26 Aug

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

฿2,581

฿2,883 total

31 Aug - 1 Sept

includes taxes & fees

7.6/10 Good! (903 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿3,027

฿3,381 total

13 Sept - 14 Sept

includes taxes & fees

8.6/10 Excellent! (1,023 reviews)

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

฿3,724

฿4,159 total

1 Sept - 2 Sept

includes taxes & fees

8.4/10 Very good! (1,010 reviews)

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

1055 South Street Pittsfield MA

฿3,986

฿4,452 total

7 Sept - 8 Sept

includes taxes & fees

9.4/10 Exceptional! (171 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿5,162

฿5,766 total

14 Sept - 15 Sept

includes taxes & fees

9.2/10 Wonderful! (1,018 reviews)

Frequently asked questions

What's the best place for a stay in Glendale?

The Yankee Inn, located 9.3 mi (14.9 km) from the heart of Glendale, is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Berkshire Mountain Lodge and Berkshires Untold. See all available top hotels, or vacation rentals in Glendale.

If I need to cancel my hotel reservation in Glendale, will I receive a refund?

Yes! You'll find that most room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Glendale.

What are some hotels with pools in Glendale?

The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG are two additional hotels that feature an on-site pool. View all hotels with pools in Glendale.

What's it like to stay in Glendale?

Visitors to Glendale will definitely find plenty to explore and enjoy. In Glendale, there are 7 hotels and other accommodation options to choose from. Find out more about Glendale.

What should I do while I'm visiting Glendale?

A favourite place to visit is Housatonic River. You'll also find Norman Rockwell Museum and Naumkeag Museum in the area. Take a look at what more there is to see and do in Expedia's Glendale guide.

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Book Hotels in Glendale on Expedia.com

Find hotels in Glendale, MA from ฿2,266

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Glendale

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Glendale hotels

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

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

3. The Red Lion Inn

4. Quality Inn Lee - Lenox South

5. Shaker Mill Inn

6. The Little Lion

7. Econo Lodge Lee - Great Barrington

8. Holiday Inn Club Vacations Oak 'n Spruce Resort

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

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

11. Travelodge by Wyndham Great Barrington Berkshires

12. Brook Farm Inn

13. Courtyard by Marriott Lenox Berkshires

14. Quality Inn Great Barrington

15. Best Western Plus Berkshire Hills Inn & Suites

16. Granville House

17. Monument Mountain Motel

18. The Inn at Stockbridge

19. The Yankee Inn

20. Devonfield Inn B&B

Top Glendale Hotel Reviews

Hotel On North

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Whitlock

The Yankee Inn

More cheap stays in Glendale

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Quality Inn Great Barrington

Best Western Plus Berkshire Hills Inn & Suites

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

The Yankee Inn

Frequently asked questions

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