Windsor Hotels from S$105

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Windsor hotel prices

Tonight
26 Dec - 27 Dec
Tomorrow night
27 Dec - 28 Dec
This weekend
27 Dec - 29 Dec
Next weekend
3 Jan - 5 Jan

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Windsor hotels

The Williams Inn
Front of property – evening/night

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (391)
"Just an overnight stay during pre Christmas lull. However, my wife and I were delighted with the excellent accommodations and sevice. They did a beautiful job creating a 21st Century version of this inn at their new location behind Main Street. I would happily stay there again. "
The price is S$251
includes taxes & fees
2 Jan - 3 Jan,2025
The Williams Inn
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is S$293
includes taxes & fees
6 Jan - 7 Jan,2025
Vacation Village in the Berkshires
Life House Berkshires
Lobby

Life House Berkshires

3.5 star property
9.0 out of 10, Wonderful, (458)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."
The price is S$135
includes taxes & fees
9 Jan - 10 Jan,2025
Life House Berkshires
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very good, (703)
"Staff was very accommodating. The pool area was quite nice and it was deep"
The price is S$150
includes taxes & fees
9 Jan - 10 Jan,2025
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Great check in experience. "
The price is S$147
includes taxes & fees
9 Jan - 10 Jan,2025
The Yankee, Trademark Collection by Wyndham
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (668)
"Very large room with a huge desk and two arm chairs. The bathroom was nice with a large walk-in shower and a rain shower head. My room faced North street, so I noticed the noise from the road, but most wouldn’t notice. Very pleased"
The price is S$197
includes taxes & fees
2 Jan - 3 Jan,2025
Hotel On North
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is S$282
includes taxes & fees
23 Jan - 24 Jan,2025
Jiminy Peak Mountain Resort
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1002)
"Stayed for a weekend wedding and it was a great location. Room was large "
The price is S$176
includes taxes & fees
26 Jan - 27 Jan,2025
Hotel Downstreet
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1002)
"nice & quiet at night with a good solid breakfast in the morning"
The price is S$192
includes taxes & fees
9 Jan - 10 Jan,2025
Hampton Inn & Suites Berkshires-Lenox
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (542)
"Staff were pleasant and helpful. Limited menu at the hotel's bistro, but two restaurants across the busy road. Pool is much smaller than it looks in the photo and hot tub was too hot. Rooms somewhat small but well laid-out."
The price is S$219
includes taxes & fees
27 Jan - 28 Jan,2025
Courtyard by Marriott Lenox Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (417)
"Good"
The price is S$278
includes taxes & fees
1 Jan - 2 Jan,2025
Berkshire Mountain Lodge
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, (1001)
"The bed was comfortable and room was nice."
The price is S$143
includes taxes & fees
9 Jan - 10 Jan,2025
Best Western Plus Berkshire Hills Inn & Suites
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (371)
"The Porches is always a treasure in the midst of chain hotels. Just the right balance of "old school" with contemporary charm. It's the place to stay in North Adams if you can get in!!"
The price is S$226
includes taxes & fees
27 Jan - 28 Jan,2025
The Porches Inn at Mass MoCA
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.6 out of 10, Good, (754)
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."
The price is S$131
includes taxes & fees
29 Dec - 30 Dec
Berkshire Inn
FairBridge Inn Express
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

2.5 star property
5.4 out of 10, (687)
"Nice room for price close by to everything fulfilled my needs"
The price is S$105
includes taxes & fees
1 Jan - 2 Jan,2025
FairBridge Inn Express
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (622)
"We enjoyed our overnight stay very much. It was conveniently located near all of our pre-holiday destinations. We will definitely be back!"
The price is S$213
includes taxes & fees
12 Jan - 13 Jan,2025
Hilton Garden Inn Lenox Pittsfield
1896 House Country Inn & Motels
Exterior

1896 House Country Inn & Motels

2.5 star property
6.6 out of 10, (405)
"It’s unique historical property. The front desk allowed us to check in three hours early due to it’s a snowy day. We had a lovely thanksgiving dinner in the restaurant belongs to the hotel. "
The price is S$118
includes taxes & fees
29 Dec - 30 Dec
1896 House Country Inn & Motels
Fairfield Inn & Suites by Marriott Williamstown
Exterior

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
8.8 out of 10, Excellent, (310)
"It was a wonderful stay, the staff was ready to help and it was a quiet clean place to do work and also go enjoy the beautiful town of Williamstown"
The price is S$231
includes taxes & fees
26 Jan - 27 Jan,2025
Fairfield Inn & Suites by Marriott Williamstown
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (704)
"Manager was helpful. The heating system was loud and although the manager tried to fix it , the noise disrupted sleep. "
The price is S$120
includes taxes & fees
2 Jan - 3 Jan,2025
Howard Johnson by Wyndham Lenox
Club Wyndham Bentley Brook
Exterior

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (493)
"Amazing location and service!"
Club Wyndham Bentley Brook
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What's the best place to stay in Windsor?

Hotel Downstreet, 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 Life House Berkshires and The Red Lion 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 Savoy Mountain State Forest, Mount Greylock State Reservation Visitor Center and Mohawk Trail State Forest. You'll also find Mount Greylock and Berkshire Athenaeum 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.