Hotels in Windsor
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Top Rated Windsor Hotels

The Yankee Inn
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
13.45 mi from city center
$127 nightly
The price is $142 total per night
$142 total
Jul 6 - Jul 7
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 tours or tickets, 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

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
13.04 mi from city center
$143 nightly
The price is $159 total per night
$159 total
Jul 7 - Jul 8
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

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
12.95 mi from city center
$181 nightly
The price is $202 total per night
$202 total
Jul 5 - Jul 6
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 Red Lion Inn
30 Main Street Stockbridge MA
20.72 mi from city center
$196 nightly
The price is $219 total per night
$219 total
Jul 6 - Jul 7
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 securing valuables, luggage storage, and dry cleaning/laundry. 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
$99 nightly
The price is $110 total per night
$110 total
Jul 5 - Jul 6
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, an ATM, and a vending machine.
Pet friendly
Parking included

Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
$183 nightly
The price is $205 total per night
$205 total
Jul 6 - Jul 7
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Free Cancellation
13.11 mi from city center
$171 nightly
The price is $191 total per night
$191 total
Jul 6 - Jul 7
Total with taxes and fees
At Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The front desk is staffed 24 hours a day to help with concierge services and securing valuables. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub

Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
Free Cancellation
Reserve now, pay when you stay
17.56 mi from city center
$135 nightly
The price is $151 total per night
$151 total
Jul 27 - Jul 28
Total with taxes and fees
At Quality Inn Lee - Lenox South, guests have access to free WiFi in public areas, express check-in, and express check-out. Onsite parking is offered for a fee. The front desk is staffed 24/7 to help with tours or tickets, and answer any questions about the accommodations. This hotel also has free newspapers.
Breakfast included
Free WiFi

Hotel On North
297 North Street Pittsfield MA
11.24 mi from city center
$249 nightly
The price is $278 total per night
$278 total
Jul 7 - Jul 8
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, luggage storage, and securing valuables. 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, a banquet hall, and an ATM.
Pet friendly
Parking included

FairBridge Inn Express
16 Cheshire Road Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
8.46 mi from city center
$63 nightly
The price is $70 total per night
$70 total
Jul 2 - Jul 3
Total with 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

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
$135 nightly
The price is $151 total per night
$151 total
Jul 5 - Jul 6
Total with 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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
19.96 mi from city center
$181 nightly
The price is $203 total per night
$203 total
Jul 22 - Jul 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 a terrace.
Pool
Air conditioning
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:
- The Yankee Inn is located 13.5 mi away, and this hotel has free breakfast, free WiFi, and free parking.
- 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.
Windsor hotels essential information
Accommodation | 982 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $278 |
Popular hotels | The Yankee Inn, Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Red Lion Inn, Red Roof Inn PLUS+ South Deerfield – Amherst, Berkshires Untold, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, Quality Inn Lee - Lenox South, Hotel On North, FairBridge Inn Express, Best Western Plus Berkshire Hills Inn & Suites, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG |
Recent Reviews

The Yankee Inn
5/5 Excellent
"We love to snow shoe.. after a chilly day of trekking through the mountains. We grab dinner locally,and cozy up to our romantic ,fully loaded room. Fire roaring,bubbles in the hot tub.. an amazing ending to and amazing day."
A verified traveler stayed at The Yankee Inn
Posted less than an hour ago
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