Olivias Overlook - West Stockbridge, Massachusetts

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Check prices for these dates

Next weekend
3 July - 5 July
In two weeks
10 July - 12 July
In one month
24 July - 26 July
In two months
21 Aug - 23 Aug

Our top choices for West Stockbridge bed & breakfast

Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AU$270
includes taxes & fees
1 July - 2 July
Shaker Mill Inn
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is AU$245
includes taxes & fees
24 June - 25 June
Wilder House Berkshires
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (188 reviews)
"beautiful inn"
United States
Maura
The price is AU$232
includes taxes & fees
6 July - 7 July
Blackberry River Inn
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (424 reviews)
"Below average B&B"
United States
Larry
The price is AU$172
includes taxes & fees
2 July - 3 July
Locust Tree Bed and Breakfast LLC
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AU$349
includes taxes & fees
7 July - 8 July
Harbour House Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (380 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AU$430
includes taxes & fees
1 July - 2 July
Chambery Inn
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AU$621
includes taxes & fees
24 June - 25 June
Devonfield Inn B&B
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is AU$318
includes taxes & fees
30 June - 1 July
Whistler's Inn Bed & Breakfast
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
8.8 out of 10, Excellent, (8 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is AU$395
includes taxes & fees
24 June - 25 June
The Berkshire Mountain Inn
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is AU$605
includes taxes & fees
24 June - 25 June
The Inn at Stockbridge
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is AU$438
includes taxes & fees
29 June - 30 June
Granville House
Suite, Private Bathroom (RedBird Suite) | View from room

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AU$571
includes taxes & fees
6 July - 7 July
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AU$1,093
includes taxes & fees
23 July - 24 July
33 Main
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AU$604
includes taxes & fees
29 June - 30 June
Experience Timeless Elegance in The Edith Wharton Room!
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is AU$338
includes taxes & fees
24 June - 25 June
The Cornell Inn, Lenox & The Berkshires
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (108 reviews)
"Very nice hotel."
United States
Erdem
The price is AU$286
includes taxes & fees
7 July - 8 July
Inn at Silver Maple Farm
Interior

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is AU$662
includes taxes & fees
29 June - 30 June
Cozy Carriage House room with a double bed and private balcony
Interior

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is AU$703
includes taxes & fees
6 July - 7 July
Elegant Carriage House room with a queen bed and private patio.
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AU$627
includes taxes & fees
24 June - 25 June
Historic Susan B. Anthony Room - Cozy & Charming Stay
Shower, towels

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is AU$604
includes taxes & fees
29 June - 30 June
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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 West Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"As always a wonderful place to stay in the Berkshires. Outstanding hospitality and warm welcomes."
John 2-night trip
Posted 2 hours ago
The Red Lion Inn

Find out more about West Stockbridge

West Stockbridge B&B information

Number of reviews
2,993
Accommodation
42 B&B
Lowest Price
AU$172
Highest Price
AU$1,093

Frequently asked questions

Searching for B&Bs in West Stockbridge?
If you're interested in something a little quirkier than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. When you want to explore some attractions in town, Stockbridge Bowl and Charles H. Baldwin & Sons are worth a stop.
How do you know if a B&B is the best choice for your stay?
B&Bs all have a unique charm — whether it's a picturesque garden or a beautiful breakfast room, the quaint details are what make bed and breakfasts a fun place to get away.
What are the best bed and breakfasts in West Stockbridge?
Here are some B&Bs in the surrounding area: Shaker Mill Inn: 9 rooms. 0.1 mi (0.2 km) from the heart of West Stockbridge. The Cornell Inn, Lenox & The Berkshires: 4.9 mi (7.9 km) from the city centre. Enjoy the free full breakfast and unique decor. Wilder House Berkshires: 5 rooms. Located 15.8 mi (25.4 km) from the core of West Stockbridge. Enjoy the free cooked breakfast and unique decor.
What's the best time of year to book my B&B in West Stockbridge?
When you're planning your getaway to West Stockbridge, make sure that you take the year-round temperatures into account. 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?
Travellers enjoy West Stockbridge for its gardens and restaurants. If you're looking to find something to do during your travels, you might consider visiting Charles H. Baldwin & Sons and Hotchkiss Mobile Studio. You should put Stockbridge Bowl and Ebenezer II Gifts and Antiques on your list if you want to see more of the area.
How can I get to and around West Stockbridge?
You can plan your excursions in and around West Stockbridge ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 7.4 mi (11.9 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 17.8 mi (28.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.