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

Find Romantic Hotels in Lenox, MA from CA $298

  • 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
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.
A dog lying on a stone wall in a forested area.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
CA $192
CA $298 total
includes taxes & fees
Oct 19 - Oct 20
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 green house with a porch, surrounded by a garden with various plants and flowers.
A covered outdoor deck with a wooden table and a mug, overlooking a forested area.
A house with a covered porch and a well-maintained garden.

2. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
CA $484
CA $916 total
includes taxes & fees
Oct 20 - Oct 21
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 red building with a green door labeled "Apartment 1," a small garden with mulch and plants, and a white car parked in the background.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.
A backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.

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 $180
CA $409 total
includes taxes & fees
Oct 18 - Oct 19
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.
CA $390
CA $843 total
includes taxes & fees
Oct 18 - Oct 19
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
"The staff was very helpful. The were lots of activities offered including the pool, hot tub, movie theater , and renting movies for free. The unit was very spacious and comfortable. We could hear the people above us stomping around a bit but that’s to be expected."
Jessica 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

8/10 Good
"Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf."
Benjamin 2-night trip
Posted 2 days ago
The Cornell Inn, Lenox & The Berkshires
The Ponds at Foxhollow

The Ponds at Foxhollow

8/10 Good
"0"
Ilya 2-night trip
Posted 4 days ago
The Ponds at Foxhollow

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.

Explore a world of travel with Expedia