Book 5 Star Hotels in Windsor
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Featured Windsor 5 Stars Hotels
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 5 - Aug 6
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.
Parking included
Free WiFi
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
12.95 mi from city center
$146 nightly
The price is $164 total per night
$164 total
Aug 24 - Aug 25
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.
Pool
Hot Tub
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
$128 nightly
The price is $143 total per night
$143 total
Aug 5 - Aug 6
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.
Pool
Parking included
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 2 - Sep 3
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 vending machine.
Pool
Hot Tub
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.
Breakfast included
Pet friendly
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
$143 nightly
The price is $159 total per night
$159 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 water dispenser, and a fireplace in the lobby.
Pet friendly
Parking included
The Williams Inn
101 Spring Street, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
16.04 mi from city center
$251 nightly
The price is $280 total per night
$280 total
Aug 11 - Aug 12
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.
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
Reserve now, pay when you stay
19.96 mi from city center
$132 nightly
The price is $147 total per night
$147 total
Sep 2 - Sep 3
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.
Pool
Air conditioning
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.
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.
Best 5 star hotels in Windsor
Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Windsor. After all, treating yourself to the finer things is what vacations are about.
What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Windsor hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.
What amenities can I expect at a 5 star hotel?
Windsor 5 star hotels and resorts typically offer luxury amenities such as:
- Gourmet restaurant
- Full-service fitness center with pool
- Luxury spa
- Welcome gifts upon arrival
- Top-of-the-line beds and linens
- Designer personal care products
- Premium cable, free Wi-Fi and device docking stations
How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Windsor with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place:
- Search hotels by price, ranging from $88 to $280
- Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
- Choose from 980 5 star hotels in Windsor!
Windsor hotels essential information
Accommodation | 980 hotels |
|---|---|
Lowest Price | $88 |
Highest Price | $280 |
Popular hotels | Hotel Downstreet, Ascend Hotel Collection, Vacation Village in the Berkshires, FairBridge Inn Express, The Williams Inn, Red Roof Inn PLUS+ South Deerfield – Amherst, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Best Western Plus Berkshire Hills Inn & Suites, Berkshire Mountain Lodge |
Recent Reviews
Hotel Downstreet, Ascend Hotel Collection
5/5 Excellent
"Everything was excellent."
A verified traveler stayed at Hotel Downstreet, Ascend Hotel Collection
Posted 9 hours ago
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