West Stockbridge Hotel Guide - Romantic Hotels in West Stockbridge, Massachusetts

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Check availability on West Stockbridge Romantic Hotels

Top West Stockbridge Romantic Hotels

Blackberry River Inn
Cozy living room with a traditional fireplace, armchairs, and a sofa, perfect for relaxing.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (124)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is €162
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (854)
"Consistently a clean room with welcoming staff."
The price is €110
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1004)
"Wonderful place to stay"
The price is €129
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham
The Nest Hudson
Relax on the outdoor deck with comfortable seating and a small table, surrounded by lush greenery.

The Nest Hudson

3.5 star property
9.6 out of 10, Exceptional, (198)
"Had a great stay"
The Nest Hudson
The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is €220
includes taxes & fees
18 Aug - 19 Aug
The Red Lion Inn
Harbour House Inn
Stunning traditional architecture with a central entrance and beautifully landscaped surroundings.

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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 €238
includes taxes & fees
18 Aug - 19 Aug
Harbour House Inn
Perfect Vacation Get Away - Historical New Marlborough
Enjoy al fresco dining and socializing in this serene outdoor patio area surrounded by lush greenery and trees.

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (55)
"Lovely place!"
The price is €279
includes taxes & fees
24 Aug - 25 Aug
Perfect Vacation Get Away - Historical New Marlborough
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Enjoy a meal at John Harvard's Restaurant & Brewery, located near a pool area with lounge chairs.

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

9.8 out of 10, Exceptional, (18)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Brook Farm Inn
Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (156)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
Brook Farm Inn
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Enjoy cooking in this kitchen with a central island, appliances, and ample counter space.

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

8.2 out of 10, Very good, (11)
"The apartment is cozy, clean, and perfect for visiting Jiminy Peak."
The price is €235
includes taxes & fees
17 Aug - 18 Aug
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We love the Red Lion. And had two excellent meals around our trips to Tanglewood concerts. We stayed at the Stevens house room 184. Sunny, sweet, fridge downstairs was helpful to store picnic items/wine. But the bed is soft and the bathtub was plastic insert which was unexpected for the cost per night, but more so the smell of mildew. "
Anonymous traveller 2-night trip
Posted 2 days ago
The Red Lion Inn

Frequently asked questions

Searching for romantic hotels in West Stockbridge?
Are you and your partner in need of a romantic holiday? 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 Hoffman's Pottery. If you'd like to stay close to a particular destination, you can sort properties by neighbourhood or distance to top landmarks, so you and your partner will get to see everything on your list.
What's the best place to stay for a couple going to West Stockbridge?
Shaker Mill Inn is a favourite B&B for couples, and features free breakfast and free WiFi.
How many romantic hotels will we be able to find in West Stockbridge?
Expedia has 11 romantic West Stockbridge hotels for you both to enjoy.
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, take a look at these details about year-round temperatures in West 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 West Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in West Stockbridge?
There's nothing better than experiencing 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 Hoffman's Pottery 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 go off without a hitch: 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 centre. If you'd like to venture out around the area, consider renting a car to explore more sights.