Chester, MA
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundable
$134 nightly
The price is $149 total per night from Jan 1 to Jan 2
$149 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,247 reviews)
Clean, quiet
Reviewed on Dec 22, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street Springfield MA
$111 nightly
The price is $125 total per night from Dec 28 to Dec 29
$125 total
Dec 28 - Dec 29
Total with taxes and 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! (1,307 reviews)
Clean room and Bed. BUT the TV definitely needs a upgrade. Very small and outdated
Reviewed on Dec 24, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$93 nightly
The price is $103 total per night from Jan 4 to Jan 5
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,000 reviews)
The bed was very comfortable. The staff was helpful and courteous
Reviewed on Dec 24, 2025
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
3 Foxhollow Drive Route 7 Lenox MA
Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club are located ...
8.6/10 Excellent! (136 reviews)
As others have said, it’s extremely well kept and clean. In the Condo and the common areas…immaculate actually. It’s very dated. It would have been nice to know we would have people above us, and the hot tub no longer exists and that was disappointing. It’s a great location and condo is well equipped. ...
Reviewed on Dec 7, 2025
Peace and quiet on the lake
Becket MA
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.4/10 Exceptional! (230 reviews)
The veiws and how peacefull it was
Reviewed on Nov 16, 2025
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough MA
Stay at this vacation home in Lanesborough. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
10/10 Exceptional! (6 reviews)
Beautiful lake house, isolated enough that you're not in the city, but close access to amenities and good food. The hot tub was an absolutely amazing experience, and Adam was thoughtful with providing instructions on how to use the firepit and outdoor heating as well. Would love to stay here ...
Reviewed on Dec 4, 2025
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
Chester Town Hall
You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area.
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- Tanglewood Music Center
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- National Shrine of the Divine Mercy
- Smith College
- Big E
- Mount Holyoke College
- Eastern States Exposition
- Bousquet Ski Area
- Holyoke Mall
- Connecticut River
- Norman Rockwell Museum
- Lee Premium Outlets
- The Mount
- Jacob's Pillow
- Historic Northampton
- Olympia Ice Center
- Naumkeag Museum
- Colonial Theater
- Berkshire Botanical Garden
- Smith College Botanic Garden
- Blandford Ski Area
- Goose Pond Reservation
- Otis Reservoir
- Berkshire Museum
- Shakespeare and Company
- Maple Corner Farm Cross Country Ski Area
- Chicopee Falls Dam