South Lee Hotel Guide - Romantic Hotels in South Lee, Massachusetts

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 South Lee Romantic Hotels

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for South Lee romantic hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1006)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is €72
includes taxes & fees
4 Jan - 5 Jan 2026
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is €88
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
United States
Lori
The price is €181
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn
Library
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is €161
includes taxes & fees
5 Jan - 6 Jan 2026
Blackberry River Inn
Terrace/patio
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (271)
"We enjoyed our stay. Excellent location to explore Western Mass!"
United States
Charles D.
The price is €182
includes taxes & fees
24 Dec - 25 Dec
Berkshire Village Carriage House - Super Private!!
Front of property
Brook Farm Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Front of property
Gedney Farm

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (132)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is €173
includes taxes & fees
30 Dec - 31 Dec
Gedney Farm
Beach
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

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)
"Great location and property. thank you"
United States
Christine P.
The price is €228
includes taxes & fees
26 Dec - 27 Dec
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Suite, Private Bathroom (RedBird Suite) | View from room
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

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 €393
includes taxes & fees
6 Jan - 7 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is €365
includes taxes & fees
25 Dec - 26 Dec
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country 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.
View all properties

Top South Lee Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

Searching for romantic hotels in South Lee?
If you and your partner need some romantic time away, we've got just the ticket. Our guests also enjoy South Lee for its restaurants and cheese shops. If you want to see some of the sights in South Lee, you might make a stop by Housatonic River or Chesterwood. If you're interested in staying close to a certain attraction, you can sort by neighbourhood 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 South Lee?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in South Lee: The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in South Lee are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in South Lee?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that South Lee has to offer. If you and your partner are interested in sampling the area's cuisine, you'll enjoy South Lee for its restaurants and cheese shops. You might consider a visit to Housatonic River or Chesterwood while you're in town.
What's the best way to get to South Lee and around town during my romantic getaway?
This information about transportation options in South Lee might help your romantic getaway go off without a hitch: The closest major airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 10.2 mi (16.4 km) from the city centre. If you'd like to venture out around the area, you may want a rental car for your journey.