Holiday rentals near Chester Town Hall
We found 550 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals within easy reach of Chester Town Hall that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Chester Town Hall
Showing deals for:16 Jan - 23 Jan
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is AU$10,816
for 7 nights, 1 home
AU$1,545 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Chester Town Hall

The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
10 out of 10
exceptional
(240 reviews)
Top rated rentals - Chester Town Hall

Lakeside in the Berkshires
10 out of 10
exceptional
(62 reviews)
This home was perfect for our family over the thanksgiving weekend. It has three levels and that provided privacy while the living area was open. Very clean, comfortable beds, a well stocked kitchen and good location for exploring Stockbridge and Lenox. Hiking trails and canoeing made it great for activities. The owner communicated answering questions promptly and left simple instructions for the home. Loved staying here.
Donna M.
Stayed Nov 2024
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value