Chesterfield, MA

Travel Guide

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
$98 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and 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 (1,000 reviews)
"Great and what we expected. Clean Room. Awesome beds. Staff was polite. Bathrooms a bit outdated, but great stay for the price."

Reviewed on Sep 28, 2025

Red Roof Inn PLUS+ West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
Total with taxes and 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! (668 reviews)
"Nice room, bathroom could use some repair, crumbling sheetrock surrounding tub enclosure, priced well"

Reviewed on Sep 30, 2025

Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
$84 nightly
The price is $96 total per night from Oct 16 to Oct 17
$96 total
Oct 16 - Oct 17
Total with taxes and fees
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,032 reviews)
"Breakfast was great with a good variety of foods available, Our room only had one chair meaning one of us had to sit on the bed. I have spinal issues and my husband has mobility issues. A second chair would have been appreciated."

Reviewed on Sep 27, 2025

Quality Inn West Springfield
See all 473 properties in Chesterfield
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.
Bear Creek Cabin

Bear Creek Cabin

Charlemont
Stay at this cabin in Charlemont. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Rowe Town Forest and Hail to the Sunrise Statue are located ...
9.8/10 Exceptional! (39 reviews)
"My family had a wonderful stay at the cabin! The home is as advertised in the pictures, and we especially enjoyed spending time by the creek in the back yard and at the fire pit."

Reviewed on Sep 9, 2025

Bear Creek Cabin
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Amherst
Stay at this apartment in Amherst. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions War Memorial and Leverett Peace ...
9/10 Wonderful! (13 reviews)
"Perfect for our needs- only 3 minutes from wedding venue down the street. The property was very clean, beautifully decorated, had plenty of parking, all sorts of games and the pool table kept everyone entertained. Also had the biggest tv in the living room I have ever seen!! We hope to stay there ..."

Reviewed on Sep 8, 2025

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
Book a stay at this family-friendly vacation home in Lenox. Enjoy private pools, laundry facilities, and in-room jetted tubs. Popular attractions Tanglewood ...
9/10 Wonderful! (29 reviews)
"The property is beautiful and the amenities were great my only issue is that the house sleeps MAYBE 13 people when the description says that is sleeps 16 in multiple places. We have"

Reviewed on Sep 29, 2025

Amore Estate - beautiful room with many places to explore and relax in.
See all properties in Chesterfield
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.

Popular places to visit

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest while you're in the area.

Chesterfield Gorge

Krug Sugarbush

You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.

Krug Sugarbush

Chesterfield Public Library

Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.

Chesterfield Public Library

Explore a world of travel with Expedia

Explore a world of travel with Expedia