Hotels with Entertainment in The Berkshires
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Hotels with Entertainment
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A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

The Berkshires Hotels with Entertainment

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your current months are November, 2026 and December, 2026.

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Our top choices for The Berkshires hotels with entertainment

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

A multi-story building with a balcony, a pond with rocks, and a tree.

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

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

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

3.5 star property

South Lee

9.2 out of 10, Wonderful, (1,002 reviews)

9.2/10

Wonderful

(1,002 reviews)

"Nice place to stay"

Michael

The price is RM474

RM474

RM608 total

includes taxes & fees

7 Dec - 8 Dec

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

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

2. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires

3.0 star property

Lenox

9.6 out of 10, Exceptional, (51 reviews)

9.6/10

Exceptional

(51 reviews)

"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"

Francis

The price is RM548

RM548

RM612 total

includes taxes & fees

15 Nov - 16 Nov

Element by Marriott Lenox Berkshires

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

A spacious living room with large windows, a fireplace, and a variety of seating options.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property

Williamstown

8.8 out of 10, Excellent, (2,835 reviews)

8.8/10

Excellent

(2,835 reviews)

"Great resort, great location very spacious."

Marcos

The price is RM326

RM326

RM409 total

includes taxes & fees

9 Nov - 10 Nov

Vacation Village in the Berkshires

A room with large windows, a red patterned rug, a wooden table with benches, and shelves with figurines.

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

An indoor swimming pool with a colorful mural on the wall, a lifeguard station, and clear pool rules posted.

4. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property

North Adams

9.0 out of 10, Wonderful, (1,003 reviews)

9.0/10

Wonderful

(1,003 reviews)

"Had a great time at this wonderful hotel."

marwan

The price is RM484

RM484

RM540 total

includes taxes & fees

22 Nov - 23 Nov

Hotel Downstreet, an Ascend Collection Hotel

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

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.

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

5. Granville House

Granville House

3.0 star property

Housatonic

10.0 out of 10, Exceptional, (110 reviews)

10/10

Exceptional

(110 reviews)

"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."

Cynthia

The price is RM1,031

RM1,031

RM1,152 total

includes taxes & fees

20 Nov - 21 Nov

Granville House

A garden with a swing set, a blue chair, and a flower bed.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

A garden with a wooden pergola, potted plants, and a lawn with chairs.

A breakfast buffet setup with cereal, milk, juice, and pastries.

6. Maple Terrace Motel

Maple Terrace Motel

2.5 star property

Williamstown

9.6 out of 10, Exceptional, (648 reviews)

9.6/10

Exceptional

(648 reviews)

"Perfect charming little hotel The couple at the front was very nice and helpful"

yeraldine

The price is RM401

RM401

RM448 total

includes taxes & fees

8 Dec - 9 Dec

Maple Terrace Motel

A wooden deck with a swing chair and a bench overlooking a lake.

A tented area with lush greenery and a dining setup.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

A modern hotel room with a bed, sofa, leather chair, and a small table.

7. Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property

Lakeville

8.2 out of 10, Very good, (325 reviews)

8.2/10

Very good

(325 reviews)

"Over eight annual visits to this hotel, it has been a wonderful stay each time."

mary

The price is RM1,019

RM1,019

RM1,172 total

includes taxes & fees

9 Nov - 10 Nov

Interlaken Inn & Resort

A modern living room with a fireplace, large windows, and a cozy seating area.

An outdoor seating area with tables and chairs, a large umbrella, and string lights.

A large building with a symmetrical facade, a central entrance with a glass door, and two smaller structures on either side.

A modern hotel room with a large bed, a desk, and a chair. There is a window with curtains, a painting of mountains, and a TV on the wall.

8. Inn At Mount Snow

Inn At Mount Snow

2.0 star property

West Dover

10.0 out of 10, Exceptional, (141 reviews)

10/10

Exceptional

(141 reviews)

"Very clean place with nice and helpful staff."

Kenneth

The price is RM522

RM522

RM574 total

includes taxes & fees

9 Nov - 10 Nov

Inn At Mount Snow

A stone fountain with water spouting from the top, surrounded by greenery and a brick building with windows in the background.

A spacious, well-lit event space with a glass ceiling, white tables, and a chandelier.

A brick building with a covered patio, a fountain, and a staircase leading to a second floor.

A person in a blue swimsuit relaxing in a hot tub with a pool in the background.

9. Simsbury Inn

Simsbury Inn

3.5 star property

Simsbury Center

9.2 out of 10, Wonderful, (323 reviews)

9.2/10

Wonderful

(323 reviews)

"Loved the 4 post beds and the linens were the nicest I have ever slept in. Lots of free parking on sight with a couple of outdoor fire pits. I would definitely stay there when we are in Simsbury"

SueEllen and Ian

The price is RM1,173

RM1,173

RM1,438 total

includes taxes & fees

9 Nov - 10 Nov

Simsbury Inn

A spacious kitchen with large windows, a bar area, and a dining setup with chairs and tables.

A large, white colonial-style house with a porch, surrounded by lush greenery and trees.

A spacious restaurant with high ceilings, patterned flooring, and multiple seating areas.

A large, white, two-story house with a central balcony and a covered porch.

10. The White House Inn

The White House Inn

3.5 star property

Wilmington

9.2 out of 10, Wonderful, (394 reviews)

9.2/10

Wonderful

(394 reviews)

"Excellent hospitality, room, beds, linens, dinner and scenery."

Teresa

The price is RM693

RM693

RM763 total

includes taxes & fees

8 Dec - 9 Dec

The White House Inn

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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The Berkshires Hotels with Entertainment

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires hotels with entertainment

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

2. Element by Marriott Lenox Berkshires

3. Vacation Village in the Berkshires

4. Hotel Downstreet, an Ascend Collection Hotel

5. Granville House

6. Maple Terrace Motel

7. Interlaken Inn & Resort

8. Inn At Mount Snow

9. Simsbury Inn

10. The White House Inn

Explore a world of travel with Expedia