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:10 Oct - 17 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 NZ$5,132
NZ$5,132
NZ$733 per night
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(19 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, Massachusetts
14% off
Price is NZ$3,871
NZ$3,871
NZ$553 per night
includes taxes & fees
Image gallery for Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Great Barrington, MA
8% off
Price is NZ$4,384
NZ$4,384
NZ$626 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 NZ$16,057
NZ$16,057
NZ$2,294 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 NZ$15,856
NZ$15,856
NZ$2,265 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 NZ$4,126
NZ$4,126
NZ$589 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 NZ$2,250
NZ$2,250
NZ$321 per night
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
8% off
Price is NZ$2,412
NZ$2,412
NZ$345 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is NZ$3,942
NZ$3,942
NZ$563 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 NZ$4,870
NZ$4,870
NZ$696 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 NZ$8,357
NZ$8,357
NZ$1,194 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 NZ$7,449
NZ$7,449
NZ$1,064 per night
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10 rating
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, Massachusetts
14% off
Price is NZ$5,933
NZ$5,933
NZ$848 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 NZ$4,166
NZ$4,166
NZ$595 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 NZ$3,108
NZ$3,108
NZ$444 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 NZ$2,776
NZ$2,776
NZ$397 per night
includes taxes & fees
Image gallery for The Maple House - Modern Retreat Near Town
1010 out of 10 rating
Exceptional
(9 reviews)
The Maple House - Modern Retreat Near Town
Lenox, MA
8% off
Price is NZ$7,686
NZ$7,686
NZ$1,098 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 NZ$2,786
NZ$2,786
NZ$398 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 NZ$8,628
NZ$8,628
NZ$1,233 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 NZ$12,542
NZ$12,542
NZ$1,792 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 NZ$6,723
NZ$6,723
NZ$960 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 NZ$3,616
NZ$3,616
NZ$517 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 NZ$8,551
NZ$8,551
NZ$1,222 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
15% off
Price is NZ$5,301
NZ$5,301
NZ$757 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chester Town Hall
Showing deals for: 4 Oct - 7 Oct
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)
The current price is NZ$1,275
NZ$1,275
for 3 nights, 1 chalet
NZ$425 per night
includes taxes & fees
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
The current price is NZ$1,213
NZ$1,213
for 3 nights, 1 villa
NZ$404 per night
includes taxes & fees
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Sleeps 10 · 4 bedrooms · 2 bathrooms
7.27.2 out of 10
Goodgood
44 reviews(44 reviews)
The current price is NZ$2,372
NZ$2,372
for 3 nights, 1 home
NZ$791 per night
includes taxes & fees
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
The current price is NZ$1,759
NZ$1,759
for 3 nights, 1 cottage
NZ$586 per night
includes taxes & fees
Romantic Berkshires Cottage - Stunning Views, Pool
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
The current price is NZ$1,671
NZ$1,671
for 3 nights, 1 cottage
NZ$557 per night
includes taxes & fees
Imagine Being Lakeside This Summer! Book Now!
Sleeps 10 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
The current price is NZ$4,208
NZ$4,208
for 3 nights, 1 home
NZ$1,403 per night
includes taxes & fees
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