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

Find Romantic Hotels in Lenox, MA from CA $295

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Check availability on Lenox Romantic Hotels

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 dog lying on a stone wall in a forested area.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
CA $190
CA $295 total
includes taxes & fees
Sep 24 - Sep 25
Berkshire Village Carriage House - Super Private!!
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
A snow-covered outdoor area with a fire pit, tables, and chairs, indicating a winter resort setting.
A hot tub with four people, wooden walls, and wall-mounted lights.
A spacious living area with a stone fireplace, comfortable seating, and a dining area.

2. 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
United States
John F.
CA $181
CA $350 total
includes taxes & fees
Sep 28 - Sep 29
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.
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 backyard with picnic tables and Adirondack chairs, a wooden fence, and a red building 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 $217
CA $392 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 modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

4. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
CA $563
CA $1,062 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
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Top Lenox Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Graham 2-night trip
Posted 23 hours ago
Vacation Village in the Berkshires
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

10/10 Excellent
"My sister-in-law and I were fortunate to reserve the last available room at Whistler's Inn Bed & Breakfast as we were first timers headed to a concert at Tanglewood. How lucky were we that we came across this beautiful place! From the minute we walked up to the front entrance, we felt like we had stepped onto a property straight out of a fairy tale in the English countryside! From the warmth of the mother/daughter inn keepers, the charming decor, the gardens still in bloom & our AMAZING (included) made to order breakfast-blueberry pancakes, eggs & sausage. Not to mention the spread of homemade breads, yogurts, cereal, juice, coffee & tea. We absolutely cannot wait to come back next year! Ten stars!"
Dana 1-night trip
Posted 2 weeks ago
Whistler's Inn Bed & Breakfast
The Ponds at Foxhollow

The Ponds at Foxhollow

10/10 Excellent
"Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely."
Susan 2-night trip
Posted 3 weeks 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.

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