A river surrounded by autumn-colored trees and a forested hill.

Find Hotels with Bars in Stockbridge, MA

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Check availability on Stockbridge Hotels with Bars

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Stockbridge hotels with a bar

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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
$191 nightly
$214 total
Nov 8 - Nov 9
Total with taxes and fees
The Red Lion Inn
A multi-story building with a balcony, a pond with rocks, and a tree.
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.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Michael
$135 nightly
$150 total
Oct 26 - Oct 27
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Two Adirondack chairs facing a river with a forested hill in the background.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.

3. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
$101 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
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.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Vandhana
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A dining area with a glass table, red walls, and framed artwork.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
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
Lenox
United Kingdom
judith
$160 nightly
$179 total
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
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.
A cozy library with bookshelves, a fireplace, and comfortable seating.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

6. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
$133 nightly
$149 total
Nov 3 - Nov 4
Total with taxes and fees
Berkshires Untold
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A hotel patio with outdoor seating and a fire pit.
A bar area with a long counter, red bar stools, and shelves with bottles and decorative items.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
$119 nightly
$133 total
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
An outdoor seating area with Adirondack chairs and a fire feature.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

8. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
United States
Francis
$135 nightly
$151 total
Nov 8 - Nov 9
Total with taxes and fees
Element by Marriott Lenox Berkshires
A building entrance with a large planter with purple flowers and a small tree.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A library with bookshelves, a television, and two armchairs.

9. Hotel On North

Hotel On North
Pittsfield
United States
Devon
$132 nightly
$148 total
Nov 10 - Nov 11
Total with taxes and fees
Hotel On North
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

10. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Stacy
$149 nightly
$167 total
Nov 23 - Nov 24
Total with taxes and fees
Little Cat Lodge
View all properties

Top Stockbridge Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Great location. We stayed one night only so we didn't enjoy the facilities. We'll come back next time!"
Eitam 1-night trip
Posted 2 hours ago
Jiminy Peak Mountain Resort
The Yankee Inn

The Yankee Inn

10/10 Excellent
"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."
Joan 2-night trip
Posted 2 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Staff were pleasant, welcoming and responsive. Suite was exceptional."
ROBERT 2-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Clean large room. Nice bathroom Walling distance to downtown and many restaurant options."
Denise 1-night trip
Posted 4 hours ago
Quality Inn Great Barrington
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Very nice Inn with a good walkable location in Lenox. Room was large & clean, bed very comfy. Breakfast was lovely in a beautiful room with a fireplace."
Kimberly 1-night trip
Posted 5 hours ago
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"
carole 1-night trip
Posted 8 hours ago
The Red Lion Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Check in & out were easy. Mint restaurant was GREAT. View from the balcony overlooking the lake was super. Same weekend for the last four years & we will be back."
Garry 2-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hotel On North

Hotel On North

10/10 Excellent
"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."
Vicki 1-night trip
Posted 3 days ago
Hotel On North

Frequently asked questions

Searching for hotels with bars in Stockbridge?
Stockbridge offers 55 hotels and other accommodations to choose from, and likely many will have a bar where you can enjoy an evening cocktail after sightseeing. While you're here, you can check out Naumkeag Museum and National Shrine of the Divine Mercy.
What are the best hotels with bars in Stockbridge?
Here are some favorite hotels with bars in and around Stockbridge: The Red Lion Inn: Hotel with 3 restaurants. Enjoy the bar, free WiFi, and free parking. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Enjoy the bar, free breakfast, and free WiFi. Vacation Village in the Berkshires: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Berkshire Mountain Lodge: Enjoy the poolside bar, 2 outdoor pools, and WiFi. Quality Inn Great Barrington: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in Stockbridge?
Consider a visit to Naumkeag Museum, National Shrine of the Divine Mercy, and Norman Rockwell Museum, and then find a cozy spot for a nightcap. Other places to see include Berkshire Botanical Garden and Stockbridge Bowl. Stockbridge is appreciated for its bars.
When is the best time to visit Stockbridge?
Visiting local bars in Stockbridge is more fun in good weather. These rainfall averages and temperatures can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Stockbridge and around the area?
Here are some of your transportation options in and around Stockbridge: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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