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

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Check availability on Lee Romantic Hotels

Our top choices for Lee romantic hotels

Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (288 reviews)
"This place was really great! Better than the photos. Clean and cute and quiet."
United States
Adam J
The price is AED 661
AED 985 total
includes taxes & fees
22 Jul - 23 Jul
Berkshire Village Carriage House - Super Private!!
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town
Lenox
10.0 out of 10, Exceptional, (82 reviews)
"Amazing property, close to town "
United States
Tricia E.
The price is AED 2,204
AED 2,814 total
includes taxes & fees
19 Jul - 20 Jul
Enjoy comfortable elegance in this secluded grand home located in town
Dining

A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (57 reviews)
"Comfortable lovely home with everything we needed to have a great weekend. "
United States
Margaret C.
The price is AED 841
AED 1,768 total
includes taxes & fees
21 Jul - 22 Jul
A roomy remodeled retreat close to MassMoCA
Indoor pool

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is AED 426
AED 915 total
includes taxes & fees
21 Jul - 22 Jul
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Property grounds

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon
10.0 out of 10, Exceptional, (94 reviews)
"Great location, quiet and beautiful. Loved the trails, picturesque drives between small towns and cozy accommodations. "
United States
Chad J.
The price is AED 1,157
AED 2,185 total
includes taxes & fees
25 Jul - 26 Jul
Lakefront Summer Stunner in New England Just 2 Hours From NYC
Beach

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is AED 566
AED 1,068 total
includes taxes & fees
26 Jul - 27 Jul
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AED 1,579
AED 2,645 total
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
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
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
Joseph 1-night trip
Posted 11 days ago
Chambery Inn

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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 Animagic Museum of Animation, 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 Animagic Museum of Animation, 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.