A town hall with a central dome and columns, surrounded by trees and people.

Find Romantic Hotels in Lenox, MA from CA $296

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Check availability on Lenox Romantic Hotels

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Lenox romantic hotels

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A house with a brick exterior, a green roof, and a driveway leading to a garage.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
CA $190
CA $296 total
includes taxes & fees
Oct 26 - Oct 27
Berkshire Village Carriage House - Super Private!!
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.
A house with a covered porch and a well-maintained garden.
A covered outdoor deck with a wooden table and a mug, overlooking a forested area.
A green house with a porch, surrounded by a garden with various plants and flowers.

2. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
CA $482
CA $913 total
includes taxes & fees
Oct 21 - Oct 22
Secluded Family Home in Serene Stockbridge Woods
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.
A backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.
A red building with a green door labeled "Apartment 1," a small garden with mulch and plants, and a white car parked in the background.

3. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
CA $171
CA $397 total
includes taxes & fees
Oct 28 - Oct 29
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with white cabinets and a built-in knife block.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.

4. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
Gorgeous Mountain Views Retreat: Family & Nature
View all properties

Top Lenox Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Amazing experience, Great for families,nearby many trails and scenic driveway! Will be back certainly"
Chui shan 1-night trip
Posted 11 hours ago
Vacation Village in the Berkshires
The Ponds at Foxhollow

The Ponds at Foxhollow

8/10 Good
"We were amazed of the space of the villa and plenty of parking, staff handled our check-in with professionalism and how the property was well maintained beautifully."
albert 2-night trip
Posted 15 hours ago
The Ponds at Foxhollow
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Great place to stay, super friendly staff. All that the Lenox and Lee had to offer isn't far. Will stay again."
Jason 1-night trip
Posted 16 hours ago
The Cornell Inn, Lenox & The Berkshires

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.

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