Olivias Overlook - West Stockbridge, Massachusetts

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Check prices for these dates

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 Aug

Our top choices for West Stockbridge motels

Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is SAR 270
SAR 296 total
includes taxes & fees
16 Jun - 17 Jun
Pleasant Valley Motel West Stockbridge
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (566 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is SAR 330
SAR 369 total
includes taxes & fees
16 Jun - 17 Jun
The Little Lion
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (469 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is SAR 247
SAR 276 total
includes taxes & fees
16 Jun - 17 Jun
Berkshire Travel Lodge
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (870 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is SAR 289
SAR 323 total
includes taxes & fees
16 Jun - 17 Jun
Monument Mountain Motel
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is SAR 530
SAR 592 total
includes taxes & fees
16 Jun - 17 Jun
Berkshire Lake Lodge
Balcony

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (226 reviews)
"Very clean. Updated "
United States
jennifer
The price is SAR 420
SAR 470 total
includes taxes & fees
16 Jun - 17 Jun
Chatham Travel Lodge
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (583 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is SAR 296
SAR 331 total
includes taxes & fees
16 Jun - 17 Jun
Travelodge by Wyndham Great Barrington Berkshires
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (102 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
The price is SAR 455
SAR 499 total
includes taxes & fees
16 Jun - 17 Jun
The Springs Motel
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (867 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is SAR 296
SAR 331 total
includes taxes & fees
16 Jun - 17 Jun
Howard Johnson by Wyndham Lenox
Classic Double Room, 2 Queen Beds, Courtyard View | Bathroom | Designer toiletries, hair dryer, towels, soap

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (48 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is SAR 515
SAR 575 total
includes taxes & fees
29 Jun - 30 Jun
East Rock Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (861 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is SAR 297
SAR 332 total
includes taxes & fees
16 Jun - 17 Jun
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (828 reviews)
"Quiet"
United States
William
The price is SAR 251
SAR 280 total
includes taxes & fees
2 Jul - 3 Jul
FairBridge Inn Express
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is SAR 342
SAR 507 total
includes taxes & fees
17 Jun - 18 Jun
Becket Motel
Egyptian cotton sheets, premium bedding, memory foam beds, desk

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (138 reviews)
"Nice "
United States
Daljit
The price is SAR 438
SAR 491 total
includes taxes & fees
16 Jun - 17 Jun
The Brooks Motel
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (667 reviews)
"Decent place.friendly, quiet"
United States
William
The price is SAR 284
SAR 317 total
includes taxes & fees
29 Jun - 30 Jun
Econo Lodge Lee - Great Barrington
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (416 reviews)
"Nice place for a stay"
United States
Jay
The price is SAR 396
SAR 443 total
includes taxes & fees
6 Jul - 7 Jul
Sunset 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 West Stockbridge Hotel Reviews

Hotel On North

Hotel On North

8/10 Good
"Aside from minor housekeeping issues like tissues and body wash ruining out, stay was great. Staff is very friendly and helpful. Hotel is well maintained and updated. Good central location in Pittsfield with lots of good restaurants and shops within walking distance."
D Tyler 4-night trip
Posted less than an hour ago
Hotel On North

Frequently asked questions

What can I expect from a motel trip to West Stockbridge?
If you can't find a motel in West Stockbridge, expand your search to find motels in the surrounding area or let Expedia help you find a similar property from more than 35 hotels and other lodging options. Simply use our search tools to filter by price per night or cost-effective amenities such as free breakfast and free airport transportation.
What's it like to stay in a motel?
At many motels, you'll often find an outdoor pool and free parking. When you stay at a motel property, you'll usually access your room from an outside corridor overlooking the parking lot. The first motels popped up in the 1920s as convenient lodging for the tired traveler taking a road trip along the major roadways of America.
What are the best motels in West Stockbridge?
Here you'll find some of our customers' top motels to book in the larger area. Pleasant Valley Motel West Stockbridge: If driving, you'll be within 11 minutes of Tanglewood Music Center. Enjoy access to the free WiFi and free parking, as well as room amenities like a microwave. Monument Mountain Motel: Free WiFi, free parking, and a picnic area are available during your stay. Central West Stockbridge is 8.8 mi (14.2 km) away. The Little Lion: Enjoy access to the picnic area, and freebies including WiFi and parking. Located 6.7 mi (10.7 km) from the heart of West Stockbridge. Howard Johnson by Wyndham Lenox: Central West Stockbridge is 7 mi (11.3 km) away. Free parking and a 24-hour front desk are available during your stay, along with room amenities like a soaking tub. Berkshire Inn: 9.3 mi (15 km) from the heart of West Stockbridge. Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking.
What can I do in West Stockbridge?
Visitors to West Stockbridge like its gardens and restaurants. As you're sightseeing around the area, be sure to enjoy all there is to see and do. Some outdoorsy places nearby include Stockbridge Bowl, Berkshire Botanical Garden, and Naumkeag Museum. You'll find these family-friendly attractions: Charles H. Baldwin & Sons, Hotchkiss Mobile Studio, and Ebenezer II Gifts and Antiques. While you're checking out the area, consider visiting Hoffman's Pottery, Tanglewood Music Center, and Norman Rockwell Museum.
What's the weather like in West Stockbridge?
Weather can make or break a roadtrip, so here's some data about year-round temperatures in West Stockbridge to help you plan yours: 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 West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What are my options for getting around West Stockbridge when staying in a motel?
We've gathered some information about local transportation options in West Stockbridge to help you navigate your stay: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 7.4 mi (11.9 km) from the city center. 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 to rent a car for your trip.

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