Find Romantic Hotels in West Stockbridge, MA

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Check availability on West Stockbridge Romantic Hotels

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top West Stockbridge Romantic Hotels

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1011)
"Great stay!"
United States
Ann
The price is AED 229
AED 256 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (974)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 341
AED 381 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is AED 519
AED 744 total
includes taxes & fees
21 Dec - 22 Dec
The Red Lion Inn
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (804)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is AED 403
AED 450 total
includes taxes & fees
1 Dec - 2 Dec
Berkshires Untold
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (160)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AED 604
AED 694 total
includes taxes & fees
1 Dec - 2 Dec
Blackberry River Inn
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
9.8 out of 10, Exceptional, (268)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
The price is AED 496
AED 775 total
includes taxes & fees
1 Dec - 2 Dec
Berkshire Village Carriage House - Super Private!!
Balcony
The Nest Hudson

The Nest Hudson

3.5 star property
Hudson
9.6 out of 10, Exceptional, (209)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
The Nest Hudson
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
Front of property
Gedney Farm

Gedney Farm

3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (132)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is AED 681
AED 747 total
includes taxes & fees
1 Dec - 2 Dec
Gedney Farm
Exterior
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, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is AED 386
AED 866 total
includes taxes & fees
3 Dec - 4 Dec
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.
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Top West Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Everything was great. "
Mosaddeq 2-night trip
Posted 6 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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Frequently asked questions

Searching for romantic hotels in West Stockbridge?
Are you looking for a romantic vacation? Our guests also enjoy West Stockbridge for its restaurants and gardens. If you want to explore the area, you might head to Stockbridge Bowl, Charles H. Baldwin & Sons, or Hotchkiss Mobile Studio. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to West Stockbridge?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in West Stockbridge: 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 West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in West Stockbridge?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all there is to see and do in West Stockbridge. Couples looking to get out in nature will enjoy West Stockbridge for its gardens. You might think about stopping by Stockbridge Bowl, Charles H. Baldwin & Sons, or Hotchkiss Mobile Studio while you're seeing the sights.
What's the best way to get to West Stockbridge and around town during my romantic getaway?
This information about transportation options in West Stockbridge might help your romantic trip get off to a smooth start: Make your way to West Stockbridge with a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport located 7.4 mi (11.9 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.