A town hall with a central dome and columns, surrounded by trees and people.

Find Romantic Hotels in Lenox, MA from CA $110

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Lenox Romantic Hotels

Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Lenox romantic hotels

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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
William
CA $149
CA $166 total
includes taxes & fees
Sep 28 - Sep 29
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
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.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Ann M
CA $195
CA $218 total
includes taxes & fees
Sep 28 - Sep 29
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".

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Drue
CA $198
CA $221 total
includes taxes & fees
Sep 28 - Sep 29
Berkshires Untold
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 modern living room with a fireplace, comfortable seating, and a large window with curtains.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
CA $217
CA $249 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.
A hotel room with a bed, a desk, and two wall-mounted lamps.
A motel with multiple rooms, a well-maintained lawn, and a stone pathway.
A kitchenette with a refrigerator, coffee maker, toaster, and bread display.

5. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Anna
CA $99
CA $110 total
includes taxes & fees
Oct 25 - Oct 26
Econo Lodge Lee - Great Barrington
A two-story building with a sign reading "Chambéry Inn".
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.
A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

6. Chambery Inn

Chambery Inn
Lee
United States
Alexandra
CA $374
CA $418 total
includes taxes & fees
Oct 27 - Oct 28
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

7. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
CA $578
CA $646 total
includes taxes & fees
Oct 25 - Oct 26
Devonfield Inn B&B
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
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.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

8. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
CA $236
CA $275 total
includes taxes & fees
Sep 27 - Sep 28
Brook Farm Inn
A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn.
A grand staircase with a wooden handrail and patterned carpet, leading to an upper floor.
A two-story building with a covered entrance and a large 'G' sign.
A grand piano in a living room with a sofa, a chandelier, and a fireplace.

9. Gateways Inn & Restaurant

Gateways Inn & Restaurant
Lenox
United States
Louise
CA $418
CA $487 total
includes taxes & fees
Sep 29 - Sep 30
Gateways Inn & Restaurant
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
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.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
CA $207
CA $302 total
includes taxes & fees
Sep 30 - Oct 1
The Red Lion Inn
View all properties

Top Lenox Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Toilet was faulty but they gave us another room. Not much variety on the breakfast"
Ron 3-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

10/10 Excellent
"My sister-in-law and I were fortunate to reserve the last available room at Whistler's Inn Bed & Breakfast as we were first timers headed to a concert at Tanglewood. How lucky were we that we came across this beautiful place! From the minute we walked up to the front entrance, we felt like we had stepped onto a property straight out of a fairy tale in the English countryside! From the warmth of the mother/daughter inn keepers, the charming decor, the gardens still in bloom & our AMAZING (included) made to order breakfast-blueberry pancakes, eggs & sausage. Not to mention the spread of homemade breads, yogurts, cereal, juice, coffee & tea. We absolutely cannot wait to come back next year! Ten stars!"
Dana 1-night trip
Posted 2 weeks ago
Whistler's Inn Bed & Breakfast
The Ponds at Foxhollow

The Ponds at Foxhollow

10/10 Excellent
"Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely."
Susan 2-night trip
Posted 3 weeks ago
The Ponds at Foxhollow

Frequently asked questions

Searching for romantic hotels in Lenox?
Are you and your partner in need of a romantic vacation? Our guests also enjoy Lenox for its museums, live music, and gardens. If you want to explore the area, you might head to Ventfort Hall Mansion and Gilded Age Museum, Shakespeare and Company, or Tanglewood Music Center. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Lenox?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Lenox: 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 Lenox are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Lenox?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all that Lenox has to offer. Couples looking for a little of everything will enjoy Lenox for its museums, live music, and gardens. You might think about visiting Ventfort Hall Mansion and Gilded Age Museum, Shakespeare and Company, or Tanglewood Music Center.
What's the best way to get to Lenox and around town during my romantic getaway?
This information about transportation options in Lenox might help your romantic getaway go off without a hitch: Make your way to Lenox with a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport located 4.7 mi (7.6 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia