Find Romantic Hotels in Stockbridge, MA

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Check availability on Stockbridge Romantic Hotels

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Top Stockbridge Romantic Hotels

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (739)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is NT$2,661
NT$2,972 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (885)
"Our stay was very pleasant "
The price is NT$3,132
NT$3,499 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (136)
"Loved everything especially Lucas and Joe💟☮️"
The price is NT$4,998
NT$5,748 total
includes taxes & fees
Oct 8 - Oct 9
Blackberry River Inn
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"great place have stayed several times, and hope to return."
The price is NT$5,170
NT$7,133 total
includes taxes & fees
Nov 2 - Nov 3
The Red Lion 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 NT$9,411
NT$11,385 total
includes taxes & fees
Oct 20 - Oct 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Nice area to visit "
The price is NT$3,914
NT$4,372 total
includes taxes & fees
Oct 5 - Oct 6
The Yankee, Trademark Collection by Wyndham
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (547)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is NT$3,137
NT$3,504 total
includes taxes & fees
Nov 3 - Nov 4
The Constance by the Lenox Collection
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (325)
"Great spot. Lots of history. "
The price is NT$5,626
NT$6,284 total
includes taxes & fees
Oct 29 - Oct 30
The Dewey
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (52)
"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!! "
The price is NT$7,977
NT$8,431 total
includes taxes & fees
Oct 7 - Oct 8
Harbour House 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 Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 2 days ago
The Red Lion Inn

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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 thing. 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'd like to stay close to a certain attraction, you can sort by neighborhood or distance to top landmarks, 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, check out these details about year-round temperatures in 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 Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Stockbridge?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover 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 go off without a hitch: If you're looking to fly to Stockbridge, the closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), located 9.6 mi (15.5 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.