Windsor Hotels from S$91

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9 Jul - 10 Jul
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10 Jul - 11 Jul
This weekend
11 Jul - 13 Jul
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18 Jul - 20 Jul

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Top 10 trending Windsor hotels

The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (486)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is S$252
includes taxes & fees
15 Jul - 16 Jul
The Constance by the Lenox Collection
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Nice place to stay. Good breakfast. "
The price is S$230
includes taxes & fees
21 Jul - 22 Jul
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is S$278
includes taxes & fees
16 Jul - 17 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Fantastic place"
The price is S$205
includes taxes & fees
7 Aug - 8 Aug
Hotel Downstreet, Ascend Hotel Collection
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is S$264
includes taxes & fees
21 Jul - 22 Jul
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold
Lobby

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (626)
"Great place stay after an evening at Tanglewood!"
The price is S$513
includes taxes & fees
12 Jul - 13 Jul
Berkshires Untold
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (738)
"A total dump !"
The price is S$102
includes taxes & fees
22 Jul - 23 Jul
FairBridge Inn Express
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (816)
"Very convenient location, downtown, short drive to local attractions "
The price is S$164
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1007)
"Great place to stay "
The price is S$170
includes taxes & fees
13 Jul - 14 Jul
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (667)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is S$248
includes taxes & fees
14 Jul - 15 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Williamstown Motel
Reception

Williamstown Motel

2.0 star property
9.4 out of 10, Exceptional, (274)
"room was spotless, staff friendly, dining easy walkable distance, although older, well maintained. good choice for overnight stay, price reasonable."
The price is S$156
includes taxes & fees
10 Jul - 11 Jul
Williamstown Motel
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"I had excellent stay at the Red Lion Inn "
The price is S$315
includes taxes & fees
23 Jul - 24 Jul
The Red Lion Inn
The Villager Motel
Exterior

The Villager Motel

2.0 star property
8.8 out of 10, Excellent, (718)
"Great quiet stay. "
The price is S$141
includes taxes & fees
16 Jul - 17 Jul
The Villager Motel
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1862)
"Very nice places "
Vacation Village in the Berkshires
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is S$270
includes taxes & fees
10 Jul - 11 Jul
Hotel On North
Howard Johnson by Wyndham Williamstown
Pool

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (848)
"The rooms were tasteful, cheerful and emaculate. We have been searching for lovely, reasonably priced accommodations for our annual trips to Williamstown and we have definitely found them here. The beds were so comfortable, the room felt spacious and the bathroom had extra perks. We will return , highly recommend!"
The price is S$157
includes taxes & fees
15 Jul - 16 Jul
Howard Johnson by Wyndham Williamstown
Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, laptop workspace, blackout curtains, iron/ironing board

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1001)
"Good Location"
The price is S$166
includes taxes & fees
20 Jul - 21 Jul
Red Roof Inn PLUS+ South Deerfield – Amherst
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (605)
"Good location. Nice for an evening after a show at Tanglewood. "
The price is S$91
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (424)
"No hot water. Limited TV, coffee was burnt tar, musty smell, hideous very dark green wall. Yikes!"
The price is S$99
includes taxes & fees
10 Jul - 11 Jul
Berkshire Travel Lodge
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (549)
"Very clean and very nice staff. Breakfast was great"
The price is S$264
includes taxes & fees
10 Jul - 11 Jul
Berkshire Valley Inn
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.
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Family-friendly hotels in Windsor you'll enjoy

Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (605)
The price is S$91
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington

Hotels with a spa in Windsor may fit your trip

Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
Chambery Inn
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.

Learn more about Windsor

Explore Windsor: its dining and more!

See all hotels in Windsor

Frequently asked questions

What's the best place to stay in Windsor?

Hotel Downstreet, Ascend Hotel Collection, located 13.6 mi (21.9 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Vacation Village in the Berkshires and The Williams Inn. See all available top hotels, or vacation rentals in Windsor.

If I need to cancel my hotel reservation in Windsor, will I receive a refund?

Yes! The majority of room reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

What are some hotels with pools in Windsor?

Vacation Village in the Berkshires: 3-star condo, 2-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and a health club. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel and Hilton Garden Inn Lenox Pittsfield are two additional hotels that feature an on-site pool. View all hotels with pools in Windsor.

What is staying in Windsor like?

Visitors can enjoy all that Windsor has to offer, including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodation options to choose from. Find out more about Windsor.

What should I do while I'm visiting Windsor?

Places to visit in the wider area include Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center and Mount Greylock. You'll also find Barrington Stage Company and Berkshire Museum in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.

What's the weather like in Windsor?

The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.