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
$134 nightly
The price is $150 total per night
$150 total
Mar 29 - Mar 30
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.
Pool
Parking included

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 29 - Mar 30
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

The Williams Inn
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
$186 nightly
The price is $208 total per night
$208 total
Mar 4 - Mar 5
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.
Pet friendly
Parking included

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
Mar 5 - Mar 6
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.
Pool
Hot Tub

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
11.47 mi from city center
$103 nightly
The price is $115 total per night
$115 total
Mar 1 - Mar 2
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.
Pool
Pet friendly

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Mar 1 - Mar 2
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

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
$125 nightly
The price is $139 total per night
$139 total
Mar 8 - Mar 9
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 a terrace.
Pool
Air conditioning

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Free Cancellation
13.55 mi from city center
$111 nightly
The price is $124 total per night
$124 total
Mar 26 - Mar 27
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

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
$87 nightly
The price is $97 total per night
$97 total
Mar 1 - Mar 2
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.
Pet friendly
Parking included

The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
20.72 mi from city center
$201 nightly
The price is $225 total per night
$225 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.

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Free Cancellation
16.94 mi from city center
$98 nightly
The price is $109 total per night
$109 total
Mar 18 - Mar 19
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

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
Mar 1 - Mar 2
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.
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.
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 | 984 hotels |
|---|---|
Lowest Price | $97 |
Highest Price | $225 |
Popular hotels | Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Williams Inn, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshires Untold, 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, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hotel On North |
Recent Reviews

Berkshire Mountain Lodge
5/5 Excellent
"Room was spotless! Kitchen was so helpful. Pool was a major hit with the kids and was warm even though it was February! They spent hours in the pool and outdoor hot tub. Will definitely stay here again!"
A verified traveler stayed at Berkshire Mountain Lodge
Posted 3 days ago
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