Romantic Hotels in Stockbridge, Massachusetts

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Check availability on Stockbridge Romantic Hotels

Tonight
Jul 3 - Jul 4
Tomorrow
Jul 4 - Jul 5
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Top Stockbridge Romantic Hotels

The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"I had excellent stay at the Red Lion Inn "
The price is P12,854
P16,878 total
includes taxes & fees
Jul 15 - Jul 16
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 P25,850
P31,271 total
includes taxes & fees
Jul 14 - Jul 15
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (111)
"Friendly staff "
The price is P9,366
P10,771 total
includes taxes & fees
Jul 15 - Jul 16
Blackberry River Inn
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (120)
"Great staff. Quiet.. and an excellent chef! Unique property and well worth it!"
Gedney Farm
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
The price is P14,777
P15,620 total
includes taxes & fees
Jul 7 - Jul 8
Harbour House Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Nice place to stay. Good breakfast. "
The price is P9,051
P10,109 total
includes taxes & fees
Jul 13 - Jul 14
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (808)
"Staff was welcoming and informative "
The price is P7,273
P8,124 total
includes taxes & fees
Jul 6 - Jul 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Gateways Inn & Restaurant
Iron/ironing board, free WiFi, bed sheets

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (188)
"Very well kept property, nice restaurant and is in a great area"
The price is P19,442
P22,689 total
includes taxes & fees
Jul 15 - Jul 16
Gateways Inn & Restaurant
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (314)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is P11,718
P13,089 total
includes taxes & fees
Jul 15 - Jul 16
The Dewey
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (475)
"All was just as advertised and the family/staff was friendly and helpful. "
The price is P9,172
P10,245 total
includes taxes & fees
Jul 10 - Jul 11
Whistler's Inn Bed & Breakfast
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.

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.
What's the best hotel for couples in Stockbridge?
The Red Lion Inn is a favorite hotel for couples, and features Frette Italian sheets and 24-hour room service. Another choice for a stay with your sweetheart is The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood.
How many romantic hotels can we expect to find in Stockbridge?
Expedia has 6 romantic Stockbridge hotels for you both to enjoy.
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.