Find Romantic Hotels in Lenox, MA

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Check availability on Lenox Romantic Hotels

Top Lenox Romantic Hotels

The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is ￥25,441
￥28,417 total
includes taxes & fees
Sep 15 - Sep 16
The Dewey
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (521)
"Great place , love it, will return"
The price is ￥22,074
￥24,657 total
includes taxes & fees
Sep 15 - Sep 16
The Constance by the Lenox Collection
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (481)
"Nice quaint out of the ordinary vacation experience. "
The price is ￥25,514
￥28,499 total
includes taxes & fees
Aug 20 - Aug 21
Whistler's Inn Bed & Breakfast
Gateways Inn & Restaurant
Room (King Room) | Iron/ironing board, free WiFi, bed sheets

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (189)
"Very well kept property, nice restaurant and is in a great area"
The price is ￥42,036
￥49,056 total
includes taxes & fees
Sep 2 - Sep 3
Gateways Inn & Restaurant
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (128)
"Great property"
Gedney Farm
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (255)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is ￥22,187
￥33,209 total
includes taxes & fees
Sep 16 - Sep 17
Berkshire Village Carriage House - Super Private!!
The Williams Inn
Front of property - evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (486)
"The property was spacious but still had a cozy feel. "
The price is ￥33,788
￥37,740 total
includes taxes & fees
Sep 7 - Sep 8
The Williams Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is ￥45,551
￥55,104 total
includes taxes & fees
Sep 3 - Sep 4
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Exterior

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

9.8 out of 10, Exceptional, (18)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
The price is ￥15,897
￥35,185 total
includes taxes & fees
Aug 20 - Aug 21
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.

Top Lenox Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Love everything about this place. If you want a true home away from home this is the place. The only miss is streaming abilities for at night, but an extra hdmi to type C cable,and we were all set!"
Andrea 2-night trip
Posted 2 days ago
Vacation Village in 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.
What's the best accommodation for a romantic getaway to Lenox?
The Cornell Inn, Lenox is a favorite B&B for couples, and features free breakfast and free WiFi. Another choice for a romantic stay is Brook Farm Inn.
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.