A street lined with historic buildings, including a Morgan House restaurant.

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Check availability on Lee Romantic Hotels

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

Our top choices for Lee romantic hotels

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

1. 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, (1,003 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 !"
United States
Gustavo
The price is AED 403
AED 450 total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A two-story building with a sign reading "Chambéry Inn".

2. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 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."
United States
Alexandra
The price is AED 681
AED 760 total
includes taxes & fees
1 Nov - 2 Nov
Chambery Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

3. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect for a travel stop-over."
United States
James
The price is AED 303
AED 338 total
includes taxes & fees
1 Dec - 2 Dec
Quality Inn Lee - Lenox South
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

4. Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (447 reviews)
"Super friendly staff, the room was very clean, even if dated. Very quiet and great for a one night stay while visiting Tanglewood."
United States
Lauren
The price is AED 298
AED 332 total
includes taxes & fees
1 Nov - 2 Nov
Sunset Inn
A room with a round table and two chairs, a window with a view of trees and a building, and an air conditioning unit.

5. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (710 reviews)
"It was super clean and safe"
United States
Fernando
The price is AED 206
AED 230 total
includes taxes & fees
22 Nov - 23 Nov
Econo Lodge Lee - Great Barrington
A hotel room with two beds, a nightstand, a lamp, and a patterned floor.

6. Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (336 reviews)
"can’t get in touch with the front desk after six. If you don’t check in at 6 go find an other place to stay"
United States
james
The price is AED 294
AED 329 total
includes taxes & fees
1 Nov - 2 Nov
Pilgrim Inn
A calm lake at dusk with a wooden dock and two chairs facing the water.

7. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is AED 401
AED 448 total
includes taxes & fees
6 Nov - 7 Nov
Berkshire Lake Lodge
Two Adirondack chairs facing a river with a forested hill in the background.

8. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The location was good for our trip."
United States
Basil
The price is AED 366
AED 409 total
includes taxes & fees
1 Dec - 2 Dec
The Yankee Inn
A building entrance with a large planter with purple flowers and a small tree.

9. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (971 reviews)
"Very nice hotel"
United States
Philip
The price is AED 422
AED 471 total
includes taxes & fees
1 Dec - 2 Dec
Hotel On North
An outdoor patio with a stone table and chairs, a grill, and a stone fireplace.

10. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is AED 3,255
AED 4,600 total
includes taxes & fees
14 Nov - 15 Nov
Maya's Garden House
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

11. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (50 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is AED 496
AED 554 total
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

12. 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, (1,001 reviews)
"Nice place to stay"
United States
Michael
The price is AED 406
AED 525 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

13. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is AED 436
AED 487 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
A spacious hotel lobby with multiple seating areas, large windows, and a television.

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
The price is AED 403
AED 450 total
includes taxes & fees
6 Nov - 7 Nov
Hampton Inn & Suites Berkshires-Lenox
A snow-covered outdoor area with a patio, seating, and a covered dining area.

15. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,001 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is AED 624
AED 716 total
includes taxes & fees
1 Nov - 2 Nov
The Cornell Inn, Lenox & The Berkshires
An indoor swimming pool with clear water, tiled floors, and a blue wall.

16. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (252 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
The price is AED 378
AED 423 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

17. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is AED 452
AED 505 total
includes taxes & fees
1 Dec - 2 Dec
East Rock Inn
Front of property

18. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is AED 1,340
AED 1,571 total
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

19. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (819 reviews)
"Nice view and location for fall color."
United States
Md
The price is AED 528
AED 589 total
includes taxes & fees
4 Nov - 5 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

20. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,247 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is AED 304
AED 421 total
includes taxes & fees
8 Nov - 9 Nov
Berkshire Mountain Lodge
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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Top Lee Hotel Reviews

Chambery Inn

Chambery Inn

10/10 Excellent
"Super welcoming and charming inn."
Daniel 2-night trip
Posted 5 days ago
Chambery Inn

Frequently asked questions

Searching for romantic hotels in Lee?
Are you looking for a romantic escape? Our guests also enjoy Lee for its shopping, museums, and restaurants. You might consider checking out some of the nearby sights and attractions such as Lee Premium Outlets, Goose Pond Reservation, or Housatonic River. If you're interested in staying close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Lee?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Lee: 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 Lee are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Lee?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that Lee has to offer. Couples looking for a little of everything will enjoy Lee for its shopping, museums, and restaurants. A visit to Lee Premium Outlets, Goose Pond Reservation, or Housatonic River might be just the ticket when you're checking out the sights.
What's the best way to get to Lee and around town during my romantic getaway?
This information about transportation options in Lee might help your romantic trip get off to a smooth start: The closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), located 8.6 mi (13.9 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

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