Book 2 Star Hotels in Windsor
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Featured Windsor 2 Stars Hotels

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
8.46 mi from city center
$71 nightly
The price is $79 total per night
$79 total
Jul 29 - Jul 30
Total includes taxes and fees
Guests of FairBridge Inn Express enjoy access to free WiFi in public areas, meeting rooms, and a business center. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has laundry facilities.
Parking included
Free WiFi

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
11.47 mi from city center
$129 nightly
The price is $144 total per night
$144 total
Jul 27 - Jul 28
Total includes 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 dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
13.04 mi from city center
$110 nightly
The price is $123 total per night
$123 total
Aug 4 - Aug 5
Total includes taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included

Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
13.58 mi from city center
$153 nightly
The price is $171 total per night
$171 total
Jul 29 - Jul 30
Total includes taxes and fees
Guests of Hotel Downstreet, Ascend Hotel Collection 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 luggage storage and securing valuables. Additional amenities include a hot tub, express check-out, and a vending machine.
Pool
Hot Tub

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
14.51 mi from city center
$127 nightly
The price is $141 total per night
$141 total
Jul 27 - Jul 28
Total includes 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 tours or tickets, dry cleaning/laundry, and securing valuables. 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

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
$199 nightly
The price is $223 total per night
$223 total
Jul 21 - Jul 22
Total includes 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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included

The Williams Inn
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
$269 nightly
The price is $301 total per night
$301 total
Aug 10 - Aug 11
Total includes taxes and fees
At The Williams Inn, guests have access to a gym, free WiFi in public areas, and a conference center. If you drive, put free parking to good use. The front desk is staffed 24/7 to help with securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include coffee/tea in a common area, a terrace, and a picnic area.
Pet friendly
Parking included

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
Reserve now, pay when you stay
19.96 mi from city center
$152 nightly
The price is $170 total per night
$170 total
Jul 22 - Jul 23
Total includes 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

Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd, South Deerfield, MA
Free Cancellation
Reserve now, pay when you stay
22.04 mi from city center
$116 nightly
The price is $130 total per night
$130 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests of Red Roof Inn PLUS+ South Deerfield – Amherst enjoy free WiFi in public areas, coffee in a common area, and an arcade/game room. If you decide to drive, there's free parking. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, an ATM, and a vending machine.
Pet friendly
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.
Windsor hotels essential information
Accommodation | 993 hotels |
---|---|
Lowest Price | $79 |
Highest Price | $301 |
Popular hotels | Vacation Village in the Berkshires, Red Roof Inn PLUS+ South Deerfield – Amherst, The Williams Inn, Hotel Downstreet, Ascend Hotel Collection, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Berkshires Untold, Holiday Inn & Suites Pittsfield-Berkshires by IHG, FairBridge Inn Express, Best Western Plus Berkshire Hills Inn & Suites |
Recent Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
5/5 Excellent
"Terrific place. Spacious, clean, comfortable."
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Posted 2 days ago