Hotels in Windsor
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Top Rated Windsor Hotels

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
$130 nightly
The price is $145 total per night
$145 total
Aug 27 - Aug 28
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.

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
12.95 mi from city center
$108 nightly
The price is $120 total per night
$120 total
Sep 7 - Sep 8
Total includes 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.

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
8.46 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Aug 10 - Aug 11
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.

The Williams Inn
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
$233 nightly
The price is $260 total per night
$260 total
Sep 7 - Sep 8
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 concierge services, securing valuables, and dry cleaning/laundry. Additional amenities include coffee/tea in a common area, a terrace, and a banquet hall.

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
$178 nightly
The price is $199 total per night
$199 total
Sep 1 - Sep 2
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 fireplace in the lobby, and a water dispenser.

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
$144 nightly
The price is $160 total per night
$160 total
Sep 7 - Sep 8
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 banquet hall.

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
$110 nightly
The price is $123 total per night
$123 total
Sep 8 - Sep 9
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.

The Red Lion Inn
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
20.72 mi from city center
$230 nightly
The price is $257 total per night
$257 total
Aug 13 - Aug 14
Total includes 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 concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this historic hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
13.45 mi from city center
$134 nightly
The price is $150 total per night
$150 total
Sep 8 - Sep 9
Total includes 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 tours or tickets, and answer any questions about the area. Additional amenities include a hot tub, meeting rooms, and conference space.

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
11.47 mi from city center
$115 nightly
The price is $128 total per night
$128 total
Sep 1 - Sep 2
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.

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
$107 nightly
The price is $120 total per night
$120 total
Sep 1 - Sep 2
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, a vending machine, and an ATM.

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
$119 nightly
The price is $133 total per night
$133 total
Sep 1 - Sep 2
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.
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.
Where is a good place to stay in Windsor?
What are some favorite hotels in Windsor?
Consider these top hotels around Windsor:
- Vacation Village in the Berkshires is located 13 mi away, and this condo has free parking, private patios, and a fitness center.
- Berkshire Mountain Lodge is located 13 mi away, and this lodge has free WiFi, free parking, and in-room kitchens.
- The Williams Inn is located 16.1 mi away, and this hotel has free WiFi, free parking, and a fitness center.
Windsor hotels essential information
Accommodation | 979 hotels |
---|---|
Lowest Price | $88 |
Highest Price | $260 |
Popular hotels | Vacation Village in the Berkshires, Berkshire Mountain Lodge, FairBridge Inn Express, The Williams Inn, Berkshires Untold, Hotel Downstreet, Ascend Hotel Collection, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Red Roof Inn PLUS+ South Deerfield – Amherst, Best Western Plus Berkshire Hills Inn & Suites |
Recent Reviews

Berkshire Mountain Lodge
5/5 Excellent
"Amazing place to stay. Can’t wait to go again. "
A verified traveler stayed at Berkshire Mountain Lodge
Posted 15 hours ago
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