Hotels near Chester Town Hall

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Dec 27 - Dec 28
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Featured Hotels near Chester Town Hall

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
Free Cancellation
14.45 mi from Chester Town Hall
$104 nightly
The price is $116 total per night
$116 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests of The Black Swan Lee - Lenox, an Ascend Collection Hotel enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Free Cancellation
14.86 mi from Chester Town Hall
$145 nightly
The price is $162 total per night
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG enjoy features like 2 indoor pools, 2 outdoor pools, and a business center. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this family-friendly hotel include a seasonal outdoor pool, an arcade/game room, and express check-out.
Pool
Air conditioning
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
15.68 mi from Chester Town Hall
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 out of 5
2 Southampton Rd Westfield MA
Free Cancellation
Reserve now, pay when you stay
15.9 mi from Chester Town Hall
$94 nightly
The price is $104 total per night
$104 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quality Inn Westfield - Springfield features free WiFi in public areas, a business center, and a computer station. If you plan to drive, free parking is available. The front desk is staffed 24/7 to help with luggage storage, tours or tickets, and securing valuables. Additional amenities include express check-out, free newspapers, and laundry facilities.
Breakfast included
Pet friendly
Hampton Inn Westfield

Hampton Inn Westfield

2.5 out of 5
39 Southampton Rd Westfield MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from Chester Town Hall
$120 nightly
The price is $134 total per night
$134 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Hampton Inn Westfield have access to an indoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. The 24-hour front desk has staff standing by to help secure valuables, and answer any questions about the accommodations. Additional amenities include a business center, coffee/tea in a common area, and a microwave in a common area.
Pool
Breakfast included
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.55 mi from Chester Town Hall
$127 nightly
The price is $142 total per night
$142 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
Renovated in 2023, Berkshires Untold offers free WiFi in public areas, coffee in a common area, and express check-in. You can take advantage of free parking if you drive. The front desk is staffed 24/7 to help with concierge services, and answer any questions about the accommodations. Additional amenities include a terrace, a fireplace in the lobby, and a water dispenser.
Pet friendly
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
16.82 mi from Chester Town Hall
$177 nightly
The price is $198 total per night
$198 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Guests of The Red Lion Inn have access to an outdoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
16.85 mi from Chester Town Hall
$93 nightly
The price is $103 total per night
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Additional amenities include a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Hot Tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
17 mi from Chester Town Hall
$108 nightly
The price is $120 total per night
$120 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf lodge include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub
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Chester Town Hall Hotels

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Chester Town Hall hotels essential information

Accommodation
1,720 hotels
Lowest Price
$103
Highest Price
$198
Popular hotels
The Black Swan Lee - Lenox, an Ascend Collection Hotel, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Quality Inn Westfield - Springfield, The Ponds at Foxhollow, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, Hampton Inn Westfield, Berkshire Mountain Lodge

Recent Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

5/5 Excellent
"Perfect for a weekend away. Stagg was friendly. Room was clean and spacious. It was everything we needed and more."
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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