Find Romantic Hotels in Lenox, MA

  • 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
25 Mar - 26 Mar
Tomorrow
26 Mar - 27 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

Our top choices for Lenox romantic hotels

Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (277 reviews)
"Property was great- clean, well equipped and a perfect spot for us to spend the night and a quick visit in the Berkshires!! "
United States
christine b.
The price is AED 496
AED 759 total
includes taxes & fees
26 Mar - 27 Mar
Berkshire Village Carriage House - Super Private!!
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 place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is AED 415
AED 882 total
includes taxes & fees
31 Mar - 1 Apr
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 Lenox Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Staff was pleasant! Clean and the restaurant was excellent!"
mark 1-night trip
Posted 3 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Explore a world of travel with Expedia

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.