Hotels with Free Parking in The Berkshires, MA
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Featured The Berkshires Hotels with Free Parking

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Free Cancellation
$119 nightly
The price is $132 total per night
$132 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
Guests of Hotel Downstreet, an Ascend Collection Hotel have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The front desk is staffed 24 hours a day to help with securing valuables and luggage storage. Additional amenities include a hot tub, express check-out, and laundry facilities.
Pool
Hot Tub

Stay Berkshires
1146 Cold Spring Road Williamstown MA
Guests of Stay Berkshires enjoy free WiFi in public areas, a seasonal outdoor pool, and a communal living room. Free parking is included with your stay. This smoke-free hotel also has a vending machine.
Pool
Breakfast included

Berkshire Inn
150 W Housatonic St Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $89 total per night
$89 total
Dec 30 - Dec 31
Total with taxes and fees
Guests of Berkshire Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a TV in a common area. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. This smoke-free motel also has a picnic area.
Pool
Parking included

Berkshire Valley Inn
2541 Hancock Rd Williamstown MA
$139 nightly
The price is $155 total per night
$155 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Berkshire Valley Inn, guests have access to free WiFi in public areas, a seasonal outdoor pool, and express check-in. A stay here includes free parking. Front-desk staff can assist with luggage storage and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Additional amenities include express check-out, a banquet hall, and a fireplace in the lobby.
Pool
Breakfast included

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Free Cancellation
$76 nightly
The price is $85 total per night
$85 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Best Western Plus Berkshire Hills Inn & Suites enjoy a gym, free WiFi in public areas, and conference space. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.
Breakfast included
Pet friendly

The Dewey
7 Hubbard Street Lenox MA
At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.
Parking included
Free WiFi

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Free Cancellation
$100 nightly
The price is $112 total per night
$112 total
Jan 13 - Jan 14, 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

Brook Farm Inn
15 Hawthorne Street Lenox MA
$165 nightly
The price is $184 total per night
$184 total
Dec 30 - Dec 31
Total with taxes and fees
Guests of Brook Farm Inn enjoy an outdoor pool, free WiFi in public areas, and conference space. A stay here includes free parking. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Other amenities at this adults-only bed & breakfast include a seasonal outdoor pool, a library, and express check-in.
Pool
Breakfast included

Chambery Inn
199 Main St Lee MA
$190 nightly
The price is $212 total per night
$212 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of Chambery Inn enjoy free WiFi in public areas, a hot tub, and spa services. A stay here includes free parking. Front-desk staff can assist with securing valuables and luggage storage. Additional amenities include express check-in, express check-out, and free newspapers.
Hot Tub
Spa

Chesapeake Inn of Lenox
210 West Street Lenox MA
At Chesapeake Inn of Lenox, guests have access to an outdoor pool, free WiFi in public areas, and an outdoor tennis court. You can take advantage of free parking, along with a free area shuttle. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this adults-only bed & breakfast include a business center, a meeting room, and free newspapers.
Pool
Breakfast included

Chestnut Lodge
75 Chestnut Street Lee MA
At Chestnut Lodge, guests have access to free WiFi in public areas, a hot tub, and a terrace. A stay here includes free parking. This smoke-free guesthouse also has a picnic area.
Hot Tub
Parking included

Courtyard by Marriott Lenox Berkshires
70 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $155 total per night
$155 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests staying at Courtyard by Marriott Lenox Berkshires enjoy an indoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include a 24-hour business center, a meeting room, and express check-in.
Pool
Parking included

Cozy Corner Motel
284 Sand Springs Rd. Rte 7 Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
Guests of Cozy Corner Motel enjoy a lazy river, free WiFi in public areas, and a business center. If you drive, take advantage of free parking. Front-desk staff can assist with luggage storage and securing valuables. Other amenities at this family-friendly motel include coffee/tea in a common area, free newspapers, and laundry facilities.
Breakfast included
Parking included

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $109 total per night
$109 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly

Quality Inn
372 Main Street Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests of Quality Inn Great Barrington enjoy a gym, free WiFi in public areas, and coffee in a common area. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a microwave in a common area, free newspapers, and a picnic area.
Breakfast included
Parking included
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.
The Berkshires hotels essential information
Accommodation | 1,084 hotels |
|---|---|
Lowest Price | $84 |
Highest Price | $212 |
Popular hotels | Hotel Downstreet, an Ascend Collection Hotel, Stay Berkshires, Berkshire Inn, Berkshire Valley Inn, Best Western Plus Berkshire Hills Inn & Suites, The Dewey, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Brook Farm Inn, Chambery Inn, Chesapeake Inn of Lenox, Chestnut Lodge, Courtyard by Marriott Lenox Berkshires, Cozy Corner Motel, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Quality Inn |
Recent Hotels with Free Parking Reviews

The Yankee, Trademark Collection by Wyndham
5/5 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 2 days ago
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