Holiday rentals near Chester Town Hall
We found 542 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:3 Oct - 10 Oct
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is AU$4,655
AU$4,655
AU$665 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(26 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is AU$8,897
AU$8,897
AU$1,271 per night
includes taxes & fees
Image gallery for Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is AU$14,173
AU$14,173
AU$2,025 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(42 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,793
AU$3,793
AU$542 per night
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
8% off
Price is AU$6,755
AU$6,755
AU$965 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is AU$2,098
AU$2,098
AU$300 per night
includes taxes & fees
Image gallery for General Williams Estate House Lenox/Stockbridge
9.89.8 out of 10 rating
Exceptional
(110 reviews)
General Williams Estate House Lenox/Stockbridge
Stockbridge, MA
8% off
Price is AU$13,997
AU$13,997
AU$2,000 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is AU$4,484
AU$4,484
AU$641 per night
includes taxes & fees
Image gallery for Amore Estate - beautiful room with many places to explore and relax in.
9.09.0 out of 10 rating
Wonderful
(24 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is AU$11,441
AU$11,441
AU$1,634 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(10 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is AU$6,728
AU$6,728
AU$961 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(16 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is AU$6,437
AU$6,437
AU$920 per night
includes taxes & fees
Image gallery for Beautiful retreat in a lake community to the enjoy the summer season.
1010 out of 10 rating
Exceptional
(39 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
9% off
Price is AU$2,555
AU$2,555
AU$365 per night
includes taxes & fees
Image gallery for Pristine Home In Becket Woods
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Pristine Home In Becket Woods
Becket, Massachusetts
14% off
Price is AU$3,589
AU$3,589
AU$513 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is AU$2,861
AU$2,861
AU$409 per night
includes taxes & fees
Image gallery for A simple kind of paradise
1010 out of 10 rating
Exceptional
(19 reviews)
A simple kind of paradise
Worthington, MA
8% off
Price is AU$2,601
AU$2,601
AU$372 per night
includes taxes & fees
Image gallery for Private river-front home with tennis court and hot tub in the Berkshire hills!
1010 out of 10 rating
Exceptional
(5 reviews)
Private river-front home with tennis court and hot tub in the Berkshire hills!
Cummington, MA
13% off
Price is AU$8,011
AU$8,011
AU$1,144 per night
includes taxes & fees
Image gallery for Contemporary Artist Sanctuary - The Studio. Artsy retreat in quiet setting.
1010 out of 10 rating
Exceptional
(5 reviews)
Contemporary Artist Sanctuary - The Studio. Artsy retreat in quiet setting.
Florence, MA
13% off
Price is AU$11,209
AU$11,209
AU$1,601 per night
includes taxes & fees
Image gallery for Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
1010 out of 10 rating
Exceptional
(65 reviews)
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
West Stockbridge, MA
12% off
Price is AU$3,322
AU$3,322
AU$475 per night
includes taxes & fees
Image gallery for Tranquil 3-BR Waterfront Retreat
1010 out of 10 rating
Exceptional
(14 reviews)
Tranquil 3-BR Waterfront Retreat
Becket, MA
8% off
Price is AU$5,362
AU$5,362
AU$766 per night
includes taxes & fees
Image gallery for * Private Berkshire Escape* Monthly Pricing Avail
9.69.6 out of 10 rating
Exceptional
(14 reviews)
* Private Berkshire Escape* Monthly Pricing Avail
Lee, MA
8% off
Price is AU$7,930
AU$7,930
AU$1,133 per night
includes taxes & fees
Image gallery for Artist's Camp on Lake Mahkeenac
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Artist's Camp on Lake Mahkeenac
Stockbridge, MA
7% off
Price is AU$3,088
AU$3,088
AU$441 per night
includes taxes & fees
Image gallery for Beautiful Timber Frame Home in the Berkshires /Available for Long Term
1010 out of 10 rating
Exceptional
(19 reviews)
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
Washington, MA
16% off
Price is AU$5,317
AU$5,317
AU$760 per night
includes taxes & fees
Image gallery for Stockbridge Home, Come Experience The Berkshires!
1010 out of 10 rating
Exceptional
(27 reviews)
Stockbridge Home, Come Experience The Berkshires!
Glendale, Massachusetts
14% off
Price is AU$4,333
AU$4,333
AU$619 per night
includes taxes & fees
Image gallery for Beautiful studio apartment close to downtown Northampton!
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Beautiful studio apartment close to downtown Northampton!
Northampton, MA
8% off
Price is AU$2,677
AU$2,677
AU$382 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Chester Town Hall
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
162 reviews(162 reviews)
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
233 reviews(233 reviews)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Sleeps 10 · 4 bedrooms · 2 bathrooms
7.27.2 out of 10
Goodgood
44 reviews(44 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
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