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 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
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 17 - Nov 18
Total with taxes and fees
The Red Lion Inn
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A café with a display case, a frozen food section, and a marketplace sign.

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
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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

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 covered outdoor area with stone pillars and a view of a road and green hills.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

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 modern living room with a fireplace, comfortable seating, and a large window with curtains.
A dining area with a glass table, red walls, and framed artwork.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

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.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a fireplace, and comfortable seating.

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 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 modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

7. 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 hotel patio with outdoor seating and a fire pit.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.
A spacious living room with a large sofa, a coffee table, and a fireplace.

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

9. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
United States
Kathleen
$219 nightly
$245 total
Nov 17 - Nov 18
Total with taxes and fees
Hampton Terrace Inn
A building entrance with a large planter with purple flowers and a small tree.
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.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

10. Hotel On North

Hotel On North
Pittsfield
United States
Devon
$137 nightly
$153 total
Nov 5 - Nov 6
Total with taxes and fees
Hotel On North
View all properties

Top Stockbridge Hotel Reviews

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 4 hours ago
Hotel On North
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great apartment. Large pool. Comfortable bed. Everything we needed for a great stay."
Alicia 1-night trip
Posted 5 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The old fashioned touches like real glasses in the rooms. The flower selections around the property. The condition of the indoor pool and whirlpool were great.The pond and surrounding land are great. Nicest motor lodge I've been to."
Erin 1-night trip
Posted 9 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Cuisine bien équipée beau site. Un peu vieillot. La porte du lave vaisselle était brisée mais il fonctionnait tout de même bien. On avait un bac avec sel et poivre et sucre en plus que des filtres et sachets à café. Un beau gros four/air fryer dans la chambre également qui était très pratique. Des couverts pour 6 personnes.Jy retournerais sans hésitation . Le lit était confortable. Les oreillers un peu moins"
Gabriel 2-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 3 days ago
Quality Inn Great Barrington

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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