Chester, MA

Travel Guide

Photo by Elizabeth Massa Peroulakis
Photo by Elizabeth Massa Peroulakis
Photo by Chris Addams
Photo by Chris Addams
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is ₩130,918 per night from Sep 28 to Sep 29
₩130,918
₩177,615 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (656 reviews)
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."

Reviewed on Sep 25, 2025

Berkshire Mountain Lodge
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
The price is ₩168,349 per night from Sep 29 to Sep 30
₩168,349
₩190,993 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,288 reviews)
"Close to the big e and the staff was good. Bartender Kim was a delight. Room was clean and spacious"

Reviewed on Sep 25, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
The price is ₩125,142 per night from Oct 1 to Oct 2
₩125,142
₩143,226 total
Oct 1 - Oct 2
includes taxes & fees
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,018 reviews)
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Reviewed on Sep 22, 2025

Red Roof Inn PLUS+ West Springfield
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.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (130 reviews)
Nice experience!
"The overall experience was great! Nice property. Ducks and geese were fun to watch off of our room’s deck."

Reviewed on Sep 21, 2025

The Ponds at Foxhollow
Westfield Vacation Rental w/ Porch, Pets Welcome!

Westfield Vacation Rental w/ Porch, Pets Welcome!

3 out of 5
Westfield
Stay at this 3-star cottage in Westfield. Enjoy free parking and air conditioning. Popular attractions Stanley Park and Woodward Center are located nearby.
Westfield Vacation Rental w/ Porch, Pets Welcome!
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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