Romantic Hotels in The Berkshires
Massachusetts
United States of America
Romantic Hotels
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A wooden signpost with signs for pastries, sandwiches, and coffee tea.

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

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Our top choices for The Berkshires romantic hotels

A hotel room with a bed, a television, a wardrobe, and a bathroom visible through an open door.

1. Garden Gables

Garden Gables

4.0 star property

Lenox

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Lovely place!"

Eyee

The price is ₹12,267

₹12,267

₹20,521 total

includes taxes & fees

9 Nov - 10 Nov

Garden Gables

Two Adirondack chairs facing a river with a forested hill in the background.

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

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

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

2. The Yankee Inn

The Yankee Inn

2.5 star property

Lenox

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

9.2/10

Wonderful

(1,002 reviews)

"The location was good for our trip."

Basil

The price is ₹11,059

₹11,059

₹12,353 total

includes taxes & fees

8 Dec - 9 Dec

The Yankee Inn

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

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

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property

Lee

9.2 out of 10, Wonderful, (1,001 reviews)

9.2/10

Wonderful

(1,001 reviews)

"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"

Gustavo

The price is ₹10,058

₹10,058

₹11,235 total

includes taxes & fees

3 Dec - 4 Dec

The Black Swan Lee - Lenox, an Ascend Collection Hotel

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

4. Berkshires Untold

Berkshires Untold

3.5 star property

Lenox

9.0 out of 10, Wonderful, (1,067 reviews)

9.0/10

Wonderful

(1,067 reviews)

"Very nice place beautiful view"

Brian

The price is ₹9,875

₹9,875

₹11,031 total

includes taxes & fees

17 Nov - 18 Nov

Berkshires Untold

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property

Lenox

9.4 out of 10, Exceptional, (1,003 reviews)

9.4/10

Exceptional

(1,003 reviews)

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

judith

The price is ₹15,967

₹15,967

₹18,314 total

includes taxes & fees

9 Nov - 10 Nov

The Cornell Inn, Lenox & The Berkshires

A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

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 covered porch with wicker furniture and hanging flower baskets.

6. The Red Lion Inn

The Red Lion Inn

3.5 star property

Stockbridge

8.8 out of 10, Excellent, (1,011 reviews)

8.8/10

Excellent

(1,011 reviews)

"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."

Lisabeth

The price is ₹14,793

₹14,793

₹21,189 total

includes taxes & fees

12 Nov - 13 Nov

The Red Lion Inn

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

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.

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.

7. Shaker Mill Inn

Shaker Mill Inn

2.5 star property

West Stockbridge

9.6 out of 10, Exceptional, (483 reviews)

9.6/10

Exceptional

(483 reviews)

"Loved the location, fireplace and vibe"

Mahadeva

The price is ₹13,617

₹13,617

₹14,938 total

includes taxes & fees

9 Nov - 10 Nov

Shaker Mill Inn

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

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

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

8. East Rock Inn

East Rock Inn

2.0 star property

Great Barrington

9.6 out of 10, Exceptional, (58 reviews)

9.6/10

Exceptional

(58 reviews)

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

Sharon

The price is ₹11,421

₹11,421

₹12,757 total

includes taxes & fees

9 Dec - 10 Dec

East Rock Inn

A wooden boat on calm water with a house in the background.

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

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

9. Prospect Berkshires

Prospect Berkshires

3.0 star property

Egremont

10.0 out of 10, Exceptional, (52 reviews)

10/10

Exceptional

(52 reviews)

"Great experience!"

Sunny

The price is ₹22,398

₹22,398

₹28,165 total

includes taxes & fees

30 Nov - 1 Dec

Prospect Berkshires

A crowded outdoor event with tents and people gathered in a grassy area.

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

A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

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

10. Chambery Inn

Chambery Inn

3.0 star property

Lee

9.6 out of 10, Exceptional, (390 reviews)

9.6/10

Exceptional

(390 reviews)

"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."

Alexandra

The price is ₹18,195

₹18,195

₹20,324 total

includes taxes & fees

16 Nov - 17 Nov

Chambery 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.

View all properties

Top The Berkshires Hotel Reviews

A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

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.

Granville House

Housatonic

10/10 Excellent

Absolutely loved my stay. Bed comfortable, linens luxurious, hosts gorgeous. Quiet and comfortable, and then some! Thanks!

Avery

Reviewed August 7, 2026Reviewed August 7, 2026

Granville House

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

A fire pit with two Adirondack chairs, a table with drinks, and a house in the background.

A room with a white door, a window, and a wall with various framed pictures.

A traditional living room with a fireplace, floral patterned sofa, and a patterned rug.

Changing Times Boutique Country Lodging

Craryville

10/10 Excellent

Our room was clean and extremely comfortable. We were met with a lovely welcome. Loretta,our host was amazing. She went the extra mile to make sure our stay was as good as it could be. Nothing was too much trouble for her including my special diet.The breakfasts were great especially the muffins!! I wish we could have stayed longer. It was a perfect place to stay for a holiday.

Diana

Reviewed July 16, 2024Reviewed July 16, 2024

Changing Times Boutique Country Lodging

Shaker Mill Inn

West Stockbridge

10/10 Excellent

Super self contained room, welcoming hosts and good meal at the Shaker Inn restaurant next door. Lovely little town. Coffee at #6 in old railway station in town a must.

Ian

Reviewed September 22, 2018Reviewed September 22, 2018

Shaker Mill Inn

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

A dining table set with a vase of flowers, a book, and cutlery.

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

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.

Brook Farm Inn

Lenox

10/10 Excellent

Beautifully presented bed and breakfast accommodation where we felt very much at home. The room was bright and cheerful and outstandingly clean. The water was hot and plentiful and the beds comfortable. Breakfast was freshly cooked and varied and the welcome was warm and informative.

Judy

Reviewed October 13, 2016Reviewed October 13, 2016

Brook Farm Inn

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lovely room, comfortable bed and a nice breakfast.

judith

Reviewed October 10, 2026Reviewed October 10, 2026

The Cornell Inn, Lenox & The Berkshires

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

A hallway with a collection of plates on the walls, leading to a staircase.

Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Nice stay with friendly welcoming staff

Martin

Reviewed May 11, 2019Reviewed May 11, 2019

The Porches Inn at Mass MoCA

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

A lovely stay at the Black Swan hotel in Lee for my birthday. Room was nice and comfortable, sweet balcony area to watch the sunset over the lake. Close to many attractions, ie, Norman Rockwell museum, outlets, pretty town, Botanical gardens and more. Would definitely go back again. Thank you

rose

Reviewed July 2, 2026Reviewed July 2, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

Lenox

10/10 Excellent

Excellent room. All very clean.

Martin

Reviewed October 15, 2025Reviewed October 15, 2025

The Yankee Inn

The Red Lion Inn

Stockbridge

8/10 Good

Great quirky old hotel in the centre of town

Michael

Reviewed September 8, 2022Reviewed September 8, 2022

The Red Lion Inn

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Search Romantic Hotels in The Berkshires

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires romantic hotels

1. Garden Gables

2. The Yankee Inn

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

4. Berkshires Untold

5. The Cornell Inn, Lenox & The Berkshires

6. The Red Lion Inn

7. Shaker Mill Inn

8. East Rock Inn

9. Prospect Berkshires

10. Chambery Inn

Top The Berkshires Hotel Reviews

Granville House

10/10 Excellent

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