Monterey Holiday Rentals, Massachusetts: Private House Rentals

A lake surrounded by autumn-colored trees reflecting on the water.

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Our top choices for Monterey hotels

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

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

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

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

Kelly

฿4,817

฿5,380 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Great Barrington

Maria Dulce

฿2,783

฿3,109 total

includes taxes & fees

10 Nov - 11 Nov

A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

A rustic barn-style venue with round tables and chairs, string lights, and a central bar area.

A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.

3. Gedney Farm

Great Barrington

Terri

฿6,763

฿7,419 total

includes taxes & fees

2 Nov - 3 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 white two-story house with a front door, windows, and a chimney.

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

4. The Old Inn On The Green

Great Barrington

Catherine

฿9,724

฿11,733 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

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

5. Quality Inn Lee - Lenox South

Lee

Christine

฿3,107

฿3,470 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

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

South Lee

Jared

฿3,923

฿5,038 total

includes taxes & fees

13 Oct - 14 Oct

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

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

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

A motel with a parking lot and several cars parked.

7. Monument Mountain Motel

Great Barrington

Andrea

฿2,007

฿2,241 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A bar with wooden floors and shelves filled with bottles.

8. The Red Lion Inn

Stockbridge

Stephan

฿5,282

฿7,565 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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.

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

Lee

Bob

฿3,962

฿4,425 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

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

10. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

฿2,649

฿2,959 total

includes taxes & fees

12 Oct - 13 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.

11. East Rock Inn

Great Barrington

ERIK

฿4,425

฿4,943 total

includes taxes & fees

11 Nov - 12 Nov

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

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

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 motel with a central entrance, a flag, and a parking area with several cars.

12. Econo Lodge Lee - Great Barrington

Lee

Anna

฿2,195

฿2,451 total

includes taxes & fees

7 Nov - 8 Nov

A picnic table with a red umbrella, surrounded by greenery and trees.

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

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

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

13. The Little Lion

Great Barrington

Lidia

฿3,470

฿3,876 total

includes taxes & fees

18 Oct - 19 Oct

A calm lake at dusk with a wooden dock and two chairs facing the water.

A small, modern room with a desk, chair, and a flat-screen TV mounted on the wall.

A two-story house with a covered porch, a driveway, and a lawn with outdoor seating.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

14. Berkshire Lake Lodge

Lee

mike

฿4,753

฿5,309 total

includes taxes & fees

1 Nov - 2 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 wooden desk, a television, a mirror, and a bathroom visible through an open door.

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'.

15. Quality Inn Great Barrington

Great Barrington

Joan

฿2,538

฿2,835 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

16. Devonfield Inn B&B

Lee

Sebastien

฿12,373

฿13,820 total

includes taxes & fees

2 Nov - 3 Nov

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

17. Granville House

Housatonic

Cynthia

฿8,517

฿9,513 total

includes taxes & fees

12 Oct - 13 Oct

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

A swimming pool with a fenced area, lounge chairs, and a warning sign.

A hotel room with two beds, a chair, and a bedside table with a phone.

18. Sunset Inn

Lee

Lauren

฿2,988

฿3,337 total

includes taxes & fees

26 Oct - 27 Oct

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

A bedroom with a large bed, a dresser, a chair, and a mirror.

19. Wilder House Berkshires

Sheffield

Mark

฿6,649

฿7,426 total

includes taxes & fees

25 Oct - 26 Oct

A two-story building with a sign reading "Chambéry Inn".

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

A cozy room with a fireplace, a sofa, a table with a bottle and glasses, and a patterned pillow.

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

20. Chambery Inn

Lee

Alexandra

฿9,053

฿10,112 total

includes taxes & fees

10 Nov - 11 Nov

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Stay near popular Monterey attractions

Lake Garfield

Commune with nature and explore the great outdoors at Lake Garfield during your travels in Monterey. While you're in the area, wander around the forests.

See properties

Bidwell House Museum

You can spend an afternoon exploring the galleries in Bidwell House Museum in Monterey. While you're in the area, stroll along the lakeside.

See properties

Mount Wilcox

Commune with nature and explore the great outdoors at Mount Wilcox during your travels in Monterey. While you're in the area, wander around the forests.

See properties

Learn more about Monterey

Explore Monterey: its forests, hiking, fishing and more!

See all hotels in Monterey

Top Monterey Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was incredible. Just need to be a little friendly at the arrival."

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

10/10 Excellent

"We requested a room on the first floor in advance. When we got there there were aware and assigned us accordingly! Staff very accommodating to our questions and food inquiries"

Berkshires Untold

10/10 Excellent

"Great, we'll run hotel"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Lovely room, comfortable bed and a nice breakfast."

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"Excellent room! Clean and good breakfast!"

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"It was fine. No breakfast that I saw"

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

the Alander

10/10 Excellent

"I wanted to sit by the firepit with my delicious Lobster Bisque from their restaurant and Reid jumped in right away and offered to start up the Firepit for me. I love the attention to the guest. It's the little things. Thank you for a good night's rest."

More cheap stays in Monterey

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,082

฿2,326 total

12 Oct - 13 Oct

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿2,538

฿2,835 total

1 Nov - 2 Nov

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

฿2,649

฿2,959 total

18 Oct - 19 Oct

includes taxes & fees

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

1055 South Street Pittsfield MA

฿3,319

฿3,708 total

8 Nov - 9 Nov

includes taxes & fees

9.2/10 Wonderful! (234 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,554

฿3,970 total

1 Nov - 2 Nov

includes taxes & fees

The Whitlock

16 Church St Lenox MA

฿4,929

฿5,506 total

2 Nov - 3 Nov

includes taxes & fees

8.4/10 Very good! (395 reviews)

Frequently asked questions

What's the best place to stay in Monterey?

Berkshire Mountain Lodge, located 16.3 mi (26.3 km) from the heart of Monterey, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Quality Inn Great Barrington and The Yankee Inn. See all available top hotels, or vacation rentals in Monterey.

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

Yes! The majority of hotel bookings are refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. 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 your booking. Filter your search by fully refundable to find flexible hotel deals in Monterey.

What are some hotels with pools in Monterey?

Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn and The Red Lion Inn are two additional hotels with an on-site pool. View all hotels with pools in Monterey.

What is staying in Monterey like?

Visitors can enjoy all that Monterey has to offer, including its forests. This city also attracts tourists with its scenic landscape. In Monterey, there are 40 hotels and other accommodation options to choose from. Find out more about Monterey.

What is there to see in Monterey?

The picturesque setting of Lake Garfield and Mount Wilcox exemplify the area's natural beauty. Additionally, you might want to add Bidwell House Museum to your itinerary. Take a look at what more there is to see and do in Expedia's Monterey guide.

What's the seasonal weather like in Monterey?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Monterey are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Monterey on Expedia.com

Find hotels in Monterey, MA from ฿2,241

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Monterey

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Monterey hotels

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

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

3. Gedney Farm

4. The Old Inn On The Green

5. Quality Inn Lee - Lenox South

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

7. Monument Mountain Motel

8. The Red Lion Inn

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

10. Travelodge by Wyndham Great Barrington Berkshires

11. East Rock Inn

12. Econo Lodge Lee - Great Barrington

13. The Little Lion

14. Berkshire Lake Lodge

15. Quality Inn Great Barrington

16. Devonfield Inn B&B

17. Granville House

18. Sunset Inn

19. Wilder House Berkshires

20. Chambery Inn

Stay near popular Monterey attractions

Lake Garfield

Bidwell House Museum

Mount Wilcox

Learn more about Monterey

Top Monterey Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

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

Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Best Western Plus Berkshire Hills Inn & Suites

Quality Inn Lee - Lenox South

the Alander

More cheap stays in Monterey

FairBridge Inn Express

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

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

The Yankee Inn

The Whitlock

Frequently asked questions

Explore a world of travel with Expedia

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