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
$126 nightly
The price is $141 total per night
$141 total
Feb 22 - Feb 23
Total with 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 concierge services and access to locker space. 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
$121 nightly
The price is $136 total per night
$136 total
Mar 15 - Mar 16
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.

The Williams Inn
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
$189 nightly
The price is $212 total per night
$212 total
Mar 11 - Mar 12
Total with 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, dry cleaning/laundry, and luggage storage. Additional amenities include coffee/tea in a common area, a terrace, and a banquet hall.

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
$93 nightly
The price is $103 total per night
$103 total
Feb 22 - Feb 23
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 tours or tickets, and answer any questions about the area. Additional amenities include a hot tub, a seasonal outdoor pool, and coffee/tea in a common area.

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
$134 nightly
The price is $150 total per night
$150 total
Feb 18 - Feb 19
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.

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
11.47 mi from city center
$102 nightly
The price is $114 total per night
$114 total
Mar 7 - Mar 8
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 dry cleaning/laundry, luggage storage, and tours or tickets. Additional amenities include a conference center, a 24-hour business center, and a computer station.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Free Cancellation
19.96 mi from city center
$130 nightly
The price is $145 total per night
$145 total
Feb 22 - Feb 23
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.

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Free Cancellation
13.55 mi from city center
$114 nightly
The price is $127 total per night
$127 total
Mar 17 - Mar 18
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.

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
$89 nightly
The price is $100 total per night
$100 total
Feb 18 - Feb 19
Total with 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.

The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
20.72 mi from city center
$183 nightly
The price is $205 total per night
$205 total
Mar 4 - Mar 5
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 concierge services, securing valuables, 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.

Hotel On North
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
11.24 mi from city center
$149 nightly
The price is $166 total per night
$166 total
Feb 19 - Feb 20
Total with taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. Front-desk staff can answer questions 24/7, and assist with securing valuables, concierge services, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include coffee/tea in a common area, an ATM, and a banquet hall.

Huttopia Berkshires
312 Kittle Rd Williamstown MA
14.94 mi from city center
$168 nightly
The price is $188 total per night
$188 total
Mar 8 - Mar 9
Total with taxes and fees
Guests staying at Huttopia Berkshires enjoy an outdoor pool, free WiFi in public areas, and a picnic area. You can put free parking to good use if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours.
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 | 989 hotels |
|---|---|
Lowest Price | $100 |
Highest Price | $212 |
Popular hotels | Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Williams Inn, The Yankee, Trademark Collection by Wyndham, Berkshires Untold, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Hotel Downstreet, an Ascend Collection Hotel, Red Roof Inn PLUS+ South Deerfield – Amherst, The Red Lion Inn, Hotel On North, Huttopia Berkshires |
Recent Reviews

Berkshire Mountain Lodge
5/5 Excellent
"Perfect location, big rooms, nice staff. "
A verified traveler stayed at Berkshire Mountain Lodge
Posted 4 days ago
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