Find Romantic Hotels in Lee, MA

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Check availability on Lee Romantic Hotels

Tonight
Dec 1 - Dec 2
Tomorrow
Dec 2 - Dec 3
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Lee Romantic Hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1014)
"Great stay!"
United States
Ann
The price is ￥9,719
￥10,856 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (975)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥15,493
￥17,306 total
includes taxes & fees
Dec 26 - Dec 27
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ￥17,057
￥19,053 total
includes taxes & fees
Dec 8 - Dec 9
Berkshires Untold
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1004)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ￥22,789
￥32,433 total
includes taxes & fees
Dec 21 - Dec 22
The Red Lion Inn
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
9.8 out of 10, Exceptional, (268)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
The price is ￥21,084
￥32,798 total
includes taxes & fees
Dec 3 - Dec 4
Berkshire Village Carriage House - Super Private!!
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ￥59,411
￥71,871 total
includes taxes & fees
Dec 15 - Dec 16
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

Gateways Inn & Restaurant

3.0 star property
Lenox
8.0 out of 10, Very Good, (192)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is ￥27,583
￥32,189 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Gateways Inn & Restaurant
Balcony
The Nest Hudson

The Nest Hudson

3.5 star property
Hudson
9.6 out of 10, Exceptional, (209)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
The Nest Hudson
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (162)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ￥25,566
￥29,401 total
includes taxes & fees
Dec 8 - Dec 9
Blackberry River 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.
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Top Lee Hotel Reviews

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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 Berkshire Mountain Country Store, Lee Premium Outlets, or Goose Pond Reservation. 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 Berkshire Mountain Country Store, Lee Premium Outlets, or Goose Pond Reservation 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.