A mountainous landscape with a lake and dense forests.

Find Romantic Hotels in West Stockbridge, MA

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Check availability on West Stockbridge Romantic Hotels

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

Our top choices for West Stockbridge romantic hotels

Terrace/patio
Coffee/tea maker, fridge, microwave, oven
Property grounds
Coffee/tea maker, fridge, microwave, oven

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
AED 496
AED 771 total
includes taxes & fees
23 Sep - 24 Sep
Berkshire Village Carriage House - Super Private!!
Beach
TV, fireplace, stereo
Coffee/tea maker, fridge, microwave, oven
Exterior

2. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
AED 566
AED 1,044 total
includes taxes & fees
23 Sep - 24 Sep
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Exterior
Interior
Coffee/tea maker, fridge, microwave, oven
Smart TV, fireplace, table tennis, books

3. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,506
AED 2,785 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
Indoor pool
Property grounds
Interior
Exterior

4. 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.
AED 354
AED 785 total
includes taxes & fees
23 Sep - 24 Sep
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
View all properties

Top West Stockbridge Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 12 hours ago
Jiminy Peak Mountain Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Gerald 1-night trip
Posted 13 hours ago
The Red Lion Inn

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 Ebenezer II Gifts and Antiques. 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 Ebenezer II Gifts and Antiques 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.

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