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Our top choices for West Stockbridge romantic hotels
1. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
10/10
Exceptional
(30 reviews)
"We had a wonderful time, we’d be happy to come back again "
"We had a wonderful time, we’d be happy to come back again "
Ofer C.
The price is AED 1,392
AED 1,392
AED 2,425 total
includes taxes & fees
16 Nov - 17 Nov
2. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski
2 Bed Berkshire Apt minutes to Jiminy Peak SkiStephentown
8.4 out of 10, Very good, (12 reviews)
8.4/10
Very good
(12 reviews)
"Great location and property. thank you"
"Great location and property. thank you"Christine P.
The price is AED 364
AED 364
AED 883 total
includes taxes & fees
9 Nov - 10 Nov
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.
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 West Stockbridge Hotel Reviews
Shaker Mill Inn
Shaker Mill InnWest Stockbridge
10/10 Excellent
This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...
This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...
Joe
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The BerkshiresLenox
10/10 Excellent
VERY friendly staff and location for area attractions.
VERY friendly staff and location for area attractions.
Lawrence
Brook Farm Inn
Brook Farm InnLenox
10/10 Excellent
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
roberta
Devonfield Inn B&B
Devonfield Inn B&BLee
10/10 Excellent
The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!
The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!
Anonymous traveler
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodStockbridge
10/10 Excellent
Diane is an absolutely lovely host--and breakfast at their table is a great experience.
Diane is an absolutely lovely host--and breakfast at their table is a great experience.
Charles
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
10/10 Excellent
A dog barking during the night
A dog barking during the night
Sheila
The Red Lion Inn
The Red Lion InnStockbridge
10/10 Excellent
This is a Classic Old Historic Inn full of Antiques, Art, & Character. The Restaurant & Music in the Basement is Very Good. Remember not to miss the Cozy Fire in the Winter or the Front Porch in the Summer.
This is a Classic Old Historic Inn full of Antiques, Art, & Character. The Restaurant & Music in the Basement is Very Good. Remember not to miss the Cozy Fire in the Winter or the Front Porch in the Summer.
Michael
Inn at Silver Maple Farm
Inn at Silver Maple FarmEast Chatham
10/10 Excellent
This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!
This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!
Michelle
The Yankee Inn
The Yankee InnLenox
10/10 Excellent
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
Colleen
Berkshires Untold
Berkshires UntoldLenox
10/10 Excellent
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
Jill
Chambery Inn
Chambery InnLee
10/10 Excellent
The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls.
Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance.
The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls.
Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance.
Elaine
Prospect Berkshires
Prospect BerkshiresEgremont
10/10 Excellent
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
Emily
Gateways Inn & Restaurant
Gateways Inn & RestaurantLenox
10/10 Excellent
The inn is a wonderful and charming grand home in Lenox. The interior has warm furnishings and the staff went out of their way to make us feel welcome. Dinner was outstanding and the wine list had many examples of fine wines from Israel. Breakfast the next morning featured a sumptuous challah french toast souffle.
The inn is a wonderful and charming grand home in Lenox. The interior has warm furnishings and the staff went out of their way to make us feel welcome. Dinner was outstanding and the wine list had many examples of fine wines from Israel. Breakfast the next morning featured a sumptuous challah french toast souffle.
Richard
Little Cat Lodge
Little Cat LodgeCopake Falls
10/10 Excellent
I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay.
I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay.
Elisabeth
East Rock Inn
East Rock InnGreat Barrington
10/10 Excellent
Great room, recently renovated. Very close to Butternut and other areas of interest.
Great room, recently renovated. Very close to Butternut and other areas of interest.
Heather
Wilder House Berkshires
Wilder House BerkshiresSheffield
10/10 Excellent
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Liliana
Changing Times Boutique Country Lodging
Changing Times Boutique Country LodgingCraryville
10/10 Excellent
Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.
Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.
Kathleen
The Old Inn On The Green
The Old Inn On The GreenGreat Barrington
10/10 Excellent
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Rishi
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.