Lodging Image

Wyndham Hotels in Chester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
14 Aug - 15 Aug
Tomorrow
15 Aug - 16 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Seamless stay from check in to check out. All the important things like cleanliness and updated bathroom with working faucets, great shower, lots of towels, etc. and unusual amenities like “two” swimming pools as well as hiking (walking) trail and ponds in the rear of the hotel property. Breakfast offerings had a big variety of foods similar to other hotels that offer full breakfast buffets. Located on a business strip with supermarkets and other useful retail stores however the hotel sits back from the road so is fairly quiet especially at night. Our room had a wide covered balcony with Adirondack chairs. Small fire-pit area out in front of the man entrance. Personally, I would have preferred a softer bed but was not uncomfortable and it did not affect my sleep. Linens and pillows were very nice, fluffy, and very clean. No funky hotel odors in the room or halls. The staff was very friendly, polite and helpful. It shows that this facility makes every effort to run a great hotel and please their customers."
Angela 2-night trip
Posted 11 hours ago
The Yankee Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good
"Shower base was very slippery-dangerous. Air-conditioning controls were poor. Thermostat was difficult to adjust and there was no ability to direct the cold air from the fan away from directly blowing on the bed. Had to move furniture to block it. Everything else was fine."
Mark 1-night trip
Posted 14 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"a very old building with tons of history and character. The room was very clean and comfortable and the staff was excellent...very friendly and accommodating."
Mark 1-night trip
Posted 14 hours ago
The Red Lion Inn
D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Spacoius rooms with very comfortable mattress. Amazing homemade breakfast with fruit and chickpea salad. Beautiful outdoor spots to sut and gather or have breakfast outside patio. Very nice pool abd hot tub. Highly recommended."
Stefan 3-night trip
Posted 19 hours ago
D. Hotel Suites & Spa
Quality Inn West Springfield

Quality Inn West Springfield

8/10 Good
"Good for 1-2 nights. Close to many restaurants."
Kevin 1-night trip
Posted 22 hours ago
Quality Inn West Springfield
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."
Linda 2-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold

Berkshires Untold

8/10 Good
"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!👍 Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh 💕and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"
Carol and Craig 1-night trip
Posted 2 days ago
Berkshires Untold
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Excellent location. Great staff. Everyone was pleasant and helpful. Breakfast every morning. Coffee available 24/7. Quiet and clean."
Angela 7-night trip
Posted 2 days ago
Tru by Hilton Chicopee Springfield
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

8/10 Good
"It was a nice place to stay for the night with comfy beds."
Malcolm 1-night trip
Posted 3 days ago
Candlewood Suites West Springfield by IHG

Explore a world of travel with Expedia