Find hotels in Windsor, MA from Rp1.283.218

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Our top choices for Windsor hotels

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (125)
Explore Glacial Potholes from this welcoming guesthouse offering snowshoeing, sledding, and snowmobiling on site. Enjoy daily housekeeping and easy access to local attractions like the Shelburne Falls Bowling Alley, with Greenfield Station just a 16-minute drive away.

"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is Rp1.130.625
Rp2.083.658 total
includes taxes & fees
5 Jan - 6 Jan 2026
Blooming Inn

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1001)
Discover convenience at this South Deerfield hotel, just minutes from Yankee Candle Village and Mount Sugarloaf State Reservation. Enjoy complimentary WiFi and parking, spotless rooms, and attentive 24-hour service, all within 15 minutes of UMass Amherst.

"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is Rp1.492.275
Rp1.666.871 total
includes taxes & fees
29 Dec - 30 Dec
Red Roof Inn PLUS+ South Deerfield – Amherst

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (806)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Centre and Berkshire Theatre Festival.

"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is Rp2.140.650
Rp2.718.569 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (196)
This motel offers a peaceful retreat with 2 hot tubs and a rejuvenating sauna. Located near Florida Free Public Library, guests praise the helpful staff and clean rooms. Enjoy free WiFi and parking during your North Adams adventure.

"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
United States
Jean
The price is Rp2.991.383
Rp3.161.898 total
includes taxes & fees
28 Dec - 29 Dec
Blue Vista Motor Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1007)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Centre. After working out in the 24-hour fitness centre, savour Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.

"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is Rp1.680.025
Rp1.876.588 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2182)
"Awesome for ski"
United States
Lazar
The price is Rp1.741.531
Rp2.129.038 total
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
Discover this charming motel in Lee with free WiFi and parking. The helpful staff ensures a welcoming stay while the seasonal outdoor pool provides refreshment. Nearby attractions include Lee Library and Tanglewood Music Centre, with hiking trails waiting for exploration.

"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is Rp1.507.500
Rp1.683.878 total
includes taxes & fees
24 Dec - 25 Dec
Sunset Inn

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
United States
john
The price is Rp1.192.845
Rp1.410.107 total
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy Corner Motel

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
Set amid East Chatham's natural beauty, this charming B&B welcomes guests with daily buffet breakfast and complimentary WiFi. Explore nearby Queechy Lake and Hand Hollow State Forest, with Albany Airport just 44 minutes away.

"Great stay, comfortable place"
United States
barry
The price is Rp2.160.750
Rp2.420.040 total
includes taxes & fees
4 Jan - 5 Jan 2026
Inn at Silver Maple Farm

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (281)
Surrounded by natural beauty, this Lenox hotel offers easy access to Tanglewood Music Centre. Explore nearby hiking and biking trails, then unwind on the terrace or garden. Free WiFi and parking enhance your Berkshires adventure.

"great location"
United States
Brian
The price is Rp2.160.750
Rp2.413.557 total
includes taxes & fees
24 Dec - 25 Dec
The Whitlock

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
Located in Lee, this inviting B&B offers kayaking adventures and a terrace with lakefront views. Wake up to a full breakfast each morning before exploring nearby attractions like The Mount and Wyndhurst Golf & Club. Helpful staff ensure a memorable stay.

"A charming inn in the center of the Berkshires."
United States
Danny
The price is Rp3.070.191
Rp3.600.873 total
includes taxes & fees
28 Dec - 29 Dec
Lakehouse Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (997)
Conveniently located a 6-minute walk from Pittsfield Intermodal Transport Centre, this hotel offers peaceful accommodation with an indoor pool. Enjoy the fitness centre, bar, and coffee shop after exploring nearby Berkshire Museum and Colonial Theatre.

"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is Rp1.552.725
Rp1.734.394 total
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is Rp2.099.138
Rp2.344.738 total
includes taxes & fees
22 Jan - 23 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
This centrally located motel has an inviting outdoor pool where you can cool off after exploring nearby attractions. Free WiFi and self parking add extra value while the helpful staff ensures a pleasant stay in clean, comfortable rooms.

"Staff was very friendly and helpful."
United States
Pamela
The price is Rp1.323.250
Rp1.478.020 total
includes taxes & fees
24 Dec - 25 Dec
Howard Johnson by Wyndham Lenox

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1003)
Experience tranquility at this welcoming hotel, just 15 minutes from Tanglewood Music Centre. Guests praise the quiet atmosphere, helpful staff, and complimentary continental breakfast. Conveniently located near Lee Library and local restaurants with easy access to shopping.

"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is Rp1.383.885
Rp1.545.799 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Lee - Lenox South

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (448)
"It is the perfect place to stay!"
United States
Darrell
The price is Rp2.410.016
Rp3.066.786 total
includes taxes & fees
22 Jan - 23 Jan 2026
The Porches Inn at Mass MoCA

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (819)
This Lenox lodge combines comfort with convenience, just a short drive from Tanglewood Music Centre. The Club Room serves delicious American cuisine, while a welcoming bar and outdoor terrace enhance your stay. Kennedy Park and Pleasant Valley Wilderness Sanctuary await nearby.

"Easiest check in and out. Great food in dining room. "
United States
William
The price is Rp1.836.588
Rp2.051.469 total
includes taxes & fees
24 Dec - 25 Dec
Berkshires Untold

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
Explore the Berkshires from this welcoming hotel with free breakfast and parking. Just a 10-minute drive to Tanglewood Music Centre, the indoor pool offers year-round relaxation. Nearby attractions include Guido's Marketplace and Bousquet Ski Area.

"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is Rp1.742.000
Rp1.945.814 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (590)
Dive into adventure at this Williamstown motel near Linear Park, offering a refreshing seasonal outdoor pool. With free breakfast, WiFi, and parking, plus nearby skiing opportunities, guests consistently praise the helpful staff, clean rooms, and overall value.

"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is Rp1.658.250
Rp1.852.215 total
includes taxes & fees
28 Dec - 29 Dec
Maple Terrace Motel

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness centre or enjoy nearby skiing options. Tanglewood Music Centre and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.

"Very friendly and good Breakfast."
United States
Jesse
The price is Rp1.279.280
Rp1.428.956 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
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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Top Windsor Hotel Reviews

More cheap stays in Windsor

Frequently asked questions

What's the best place to stay in Windsor?
Vacation Village in the Berkshires, located 13 mi (21 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 The Williams Inn and Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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 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 Swift River. You'll also find Mount Greylock and Barrington Stage Company 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.

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