A river surrounded by autumn-colored trees and a forested hill.

Find Romantic Hotels in Stockbridge, MA from CA $300

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Check availability on Stockbridge Romantic Hotels

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Stockbridge romantic hotels

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.
A green house with a porch, surrounded by a garden with various plants and flowers.
A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.
A house with a covered porch and a well-maintained garden.

1. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
CA $487
CA $922 total
includes taxes & fees
Oct 20 - Oct 21
Secluded Family Home in Serene Stockbridge Woods
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A house with a brick exterior, a green roof, and a driveway leading to a garage.
A dog lying on a stone wall in a forested area.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.

2. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
CA $193
CA $300 total
includes taxes & fees
Oct 19 - Oct 20
Berkshire Village Carriage House - Super Private!!
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
A red building with a green door labeled "Apartment 1," a small garden with mulch and plants, and a white car parked in the background.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.
A backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.

3. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
CA $165
CA $394 total
includes taxes & fees
Oct 15 - Oct 16
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.
A modern kitchen with white cabinets and a built-in knife block.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.

4. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
CA $443
CA $911 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
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Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This was a fantastic property to end our New England trip!"
Adrianne 2-night trip
Posted 6 hours ago
Vacation Village in the Berkshires
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."
Alexandra 1-night trip
Posted 1 day ago
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We had a nice stay at the Red Lion Inn. Our room was clean and had a fireplace, but did not have a mini-refrigerator and the TV was placed to the side of the bed. The restaurant charged a lot ($65 for a filet mignon entree) and the food was not up to that price. The bread and salad were a la carte. The whole place seemed in need of a refresh."
Patricia 1-night trip
Posted 1 day ago
The Red Lion Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort

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.

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