Hotels in Windsor
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Top Rated Windsor Hotels

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
12.95 mi from city center
$113 nightly
The price is $126 total per night
$126 total
May 24 - May 25
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

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
$111 nightly
The price is $124 total per night
$124 total
May 25 - May 26
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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included

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
May 18 - May 19
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 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, an Ascend Collection Hotel
40 Main St North Adams MA
Free Cancellation
13.55 mi from city center
$152 nightly
The price is $170 total per night
$170 total
May 24 - May 25
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 luggage storage and securing valuables. Additional amenities include a hot tub, express check-out, and laundry facilities.
Pool
Hot Tub

The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
20.72 mi from city center
$186 nightly
The price is $208 total per night
$208 total
May 27 - May 28
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. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this golf hotel include meeting rooms, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa

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
$104 nightly
The price is $116 total per night
$116 total
May 31 - Jun 1
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

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
13.51 mi from city center
$119 nightly
The price is $133 total per night
$133 total
May 25 - May 26
Total with taxes and fees
Guests staying at Hampton Inn & Suites Berkshires-Lenox enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and litter boxes. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast 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
$134 nightly
The price is $149 total per night
$149 total
May 20 - May 21
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Free Cancellation
16.94 mi from city center
$123 nightly
The price is $138 total per night
$138 total
May 25 - May 26
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

The Williams Inn
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
$264 nightly
The price is $294 total per night
$294 total
May 18 - May 19
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 luggage storage, securing valuables, and concierge services. Additional amenities include coffee/tea in a common area, a terrace, and wedding services.
Pet friendly
Parking included

Hotel On North
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
11.24 mi from city center
$159 nightly
The price is $178 total per night
$178 total
Jun 16 - Jun 17
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 tours or tickets, securing valuables, 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

The Yankee Inn
461 Pittsfield Rd Lenox MA
13.45 mi from city center
$109 nightly
The price is $122 total per night
$122 total
May 18 - May 19
Total with taxes and fees
The Yankee Inn features an indoor pool, an outdoor pool, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with concierge services, and answer any questions about the area. Additional amenities include free WiFi in public areas, a hot tub, and a seasonal outdoor pool.
Pool
Hot Tub
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:
- Berkshire Mountain Lodge is located 13 mi away, and this lodge has free WiFi, free parking, and in-room kitchens.
- Berkshires Untold is located 14.4 mi away, and this lodge has free WiFi, free parking, and concierge services.
- Vacation Village in the Berkshires is located 13 mi away, and this condo has free parking, private patios, and a fitness center.
Windsor hotels essential information
Accommodation | 998 hotels |
|---|---|
Lowest Price | $116 |
Highest Price | $294 |
Popular hotels | Berkshire Mountain Lodge, Berkshires Untold, Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, The Red Lion Inn, Red Roof Inn PLUS+ South Deerfield – Amherst, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, The Williams Inn, Hotel On North, The Yankee Inn |
Recent Reviews

Red Roof Inn PLUS+ South Deerfield – Amherst
2/5 Poor
"We arrived around 8:30 pm and there was nobody at the front desk. We rang the bell and called front desk only to hear it ring and ring. The lady finally came back about 15 minutes later. Not acceptable and very dissapointing"
A verified traveler stayed at Red Roof Inn PLUS+ South Deerfield – Amherst
Posted less than an hour ago
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