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Top Stockbridge Romantic Hotels

Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 4.057.900 ₫
5.710.045 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Red Lion Inn
Business centre
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 Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"
United States
Carol Anne
The price is 10.063.592 ₫
12.174.087 ₫ total
includes taxes & fees
30 Nov - 1 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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, (958)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
The price is 2.324.070 ₫
2.596.002 ₫ total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1003)
"Great stay!"
United States
Ann
The price is 2.608.650 ₫
2.913.783 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (799)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is 2.441.222 ₫
2.726.845 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Berkshires Untold
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (157)
"Very good breakfast.excellent waiter.love the atmosphere."
United States
Marc
The price is 4.330.622 ₫
4.980.216 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Blackberry River Inn
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
Harbour House Inn
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had a wonderful stay. We are so glad we chose this inn. The location is superb…a five-minute walk to the center of Lenox! It is a beautiful inn with a lot of charm, and the staff is warm and friendly. We loved our large room too! Definitely plan on staying here again when we come back to the area! "
United States
Itzhak
The price is 3.564.365 ₫
3.981.486 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Whistler's Inn Bed & Breakfast
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
Gedney Farm
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 Stockbridge Hotel Reviews

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Frequently asked questions

Searching for romantic hotels in Stockbridge?
If you and your partner need a romantic escape, we've got just the ticket. Our guests also enjoy Stockbridge for its bars and historic landmarks. You might consider checking out some of the nearby sights and attractions such as Naumkeag Museum, National Shrine of the Divine Mercy or Norman Rockwell Museum. If you're interested in staying near a certain attraction, you can sort by neighbourhood 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 Stockbridge?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Stockbridge: The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Stockbridge?
There's nothing better than experiencing a new destination with your sweetheart, so consider checking out all there is to see and do in Stockbridge. If you're hoping to see some of the area's cultural attractions, you'll enjoy Stockbridge for its historic landmarks. You might think about stopping by Naumkeag Museum, National Shrine of the Divine Mercy or Norman Rockwell Museum while you're seeing the sights.
What's the best way to get to Stockbridge and around town during my romantic getaway?
These transportation options in Stockbridge might help your romantic trip get off to a smooth start: If you're looking to fly to Stockbridge, the closest major airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 9.6 mi (15.5 km) from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.