Photo by Elizabeth Massa Peroulakis

Search Inns in Chester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 4 Inns in Chester with updated reviews, rates, and availability.

Apple Tree Inn

3.0 star property
8.4 out of 10, Very Good, (270)
"This historic place has all the charm and character! Incredibly close to Tanglewood, The Mount, and downtown Lenox, you can’t find a better spot. The 1800’s building has charm, just be aware there are no elevators in the main building (this is not a problem to me!) the property is gorgeous, views stunning, full of character, and the restaurant was delicious. "
The price is SAR 549
SAR 613 total
includes taxes & fees
26 Dec - 27 Dec
Apple Tree Inn

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (80)
"2nd stay here, even nicer than the first (and the first was amazing!). Can’t wait to return to this enchanting inn! "
The price is SAR 995
SAR 1,157 total
includes taxes & fees
1 Jan - 2 January 2025
The Old Inn On The Green

Kemble Inn

3.5 star property
8.8 out of 10, Excellent, (31)
"wonderfully restored old mansion. Rooms were charming... nicely designed. In fact the entire facility has been thoughtfully brought into today's design standards. Very accomodating staff... although many appeared to be a training mode. Need to improve the professionalism a bit. They have a new general manager (had only been there about 2 weeks when we visited)... seems he has a number of things on his agenda that will improve the property even more. Food was good... but not wonderful. ...
Kemble Inn

The Kemble Berkshires

2.0 star property
The Kemble Berkshires
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chester

Cozy Berkshires Vacation Rental Near Hiking!

10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 548
SAR 839 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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.