Find hotels in Windsor, MA from ฿2,782

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4 Jan - 5 Jan
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Our top choices for Windsor hotels

Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is ฿13,398
฿14,697 total
includes taxes & fees
5 Jan - 6 Jan
Inn at Kenmore Hall
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (351)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ฿2,963
฿3,310 total
includes taxes & fees
5 Jan - 6 Jan
The Central Downtown Inn & Suites
Single Room | In-room safe, desk, free WiFi, bed sheets
Blue Vista Motor Lodge

Blue Vista Motor Lodge

Blue Vista Motor Lodge
2.0 star property
North Adams
9.8 out of 10, Exceptional, (197)
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 ฿5,630
฿5,951 total
includes taxes & fees
5 Jan - 6 Jan
Blue Vista Motor Lodge
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841)
This peaceful motel offers a seasonal outdoor pool and clean rooms just 15 minutes from Tanglewood Music Centre. Close to Colonial Theatre and Berkshire Museum, with free WiFi and parking. Guests praise the helpful staff and quiet, relaxing atmosphere.
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ฿2,711
฿3,028 total
includes taxes & fees
19 Jan - 20 Jan
Berkshire Inn
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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, (1002)
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 ฿2,408
฿2,689 total
includes taxes & fees
7 Jan - 8 Jan
Best Western Plus Berkshire Hills Inn & Suites
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (660)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness centre. Enjoy meals at Jae's Asian Fusion restaurant and bar, plus in-room refrigerators and microwaves. Nearby attractions include Herman Melville's Arrowhead and Guido's Marketplace.
" Nice staff - beautiful hotel!"
United States
MARY
The price is ฿4,031
฿4,503 total
includes taxes & fees
9 Jan - 10 Jan
Hilton Garden Inn Lenox Pittsfield
Suite, 2 Bedrooms | Frette Italian sheets, premium bedding, down duvets, minibar
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
3.5 star property
North Adams
9.4 out of 10, Exceptional, (451)
"It is the perfect place to stay!"
United States
Darrell
The price is ฿4,528
฿5,763 total
includes taxes & fees
2 Feb - 3 Feb
The Porches Inn at Mass MoCA
Exterior
Howard Johnson by Wyndham Lenox

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 ฿2,490
฿2,782 total
includes taxes & fees
5 Jan - 6 Jan
Howard Johnson by Wyndham Lenox
Front of property – evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (811)
Minutes from Barrington Stage Company and Berkshire Athenaeum, this hotel offers comfortable rooms and attentive service. Just a 2-minute walk from Pittsfield Intermodal Transport Centre, enjoy room service and the convenient city centre location.
"Clean room and staff was super friendly"
United States
Yuen
The price is ฿4,697
฿5,247 total
includes taxes & fees
7 Jan - 8 Jan
Hotel On North
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1006)
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.
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is ฿3,089
฿3,451 total
includes taxes & fees
9 Jan - 10 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Aerial view
Inn at Silver Maple Farm

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 ฿4,067
฿4,555 total
includes taxes & fees
5 Jan - 6 Jan
Inn at Silver Maple Farm
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (805)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.
"great stall and friendly pet friendly place"
United States
bonnie
The price is ฿3,111
฿4,179 total
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge
Outdoor pool
Berkshire Travel Lodge

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (461)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is ฿2,128
฿2,383 total
includes taxes & fees
5 Jan - 6 Jan
Berkshire Travel Lodge
Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
Unwind at this cosy Cheshire inn offering free WiFi and parking. Explore nearby Mount Greylock State Reservation or catch a show at Adams Theatre, then return to comfortable accommodation just 16 minutes from Pittsfield Station.
"Nice place for a weekend away."
United States
Gregory
The price is ฿6,778
฿7,164 total
includes taxes & fees
7 Jan - 8 Jan
Harbour House Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (72)
Located 10 minutes from Tanglewood Music Centre, this hotel provides complimentary breakfast, WiFi, and parking. After exploring nearby attractions, unwind in the indoor pool or soothing hot tub for a peaceful end to your Pittsfield adventure.
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is ฿3,863
฿4,315 total
includes taxes & fees
8 Jan - 9 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
This charming bed and breakfast in Lenox offers a complimentary full breakfast daily. Enjoy free WiFi and parking while staying minutes from Lenox Library and The Bookshop. Pittsfield Municipal Airport is just an 11-minute drive away.
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ฿12,617
฿14,094 total
includes taxes & fees
18 Jan - 19 Jan
33 Main
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (988)
Experience mountain magic at this ski-in/ski-out resort featuring 2 restaurants, 2 bars, and an outdoor pool. Condos include microwaves and DVD players, while the property offers ski storage, rentals, and lessons just steps from Mountain Coaster.
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ฿6,904
฿7,712 total
includes taxes & fees
5 Jan - 6 Jan
Jiminy Peak Mountain Resort
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
Devonfield Inn B&B offers massages, free breakfast, and complimentary WiFi near Greenock Country Club. The charming property features a lovely terrace and garden, with free parking for easy exploration of nearby attractions.
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
Peaceful accommodation in a safe location make this motel a smart choice for travellers. Free perks include WiFi and self parking, while the 24-hour front desk ensures assistance anytime. Nearby attractions and skiing opportunities add adventure to your restful stay.
"Room spotless and staff helpful."
United States
William
The price is ฿2,525
฿2,821 total
includes taxes & fees
18 Jan - 19 Jan
FairBridge Inn Express
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
Set in Lee, this B&B offers serene escapes with an outdoor pool and rejuvenating massages. Explore nearby National Shrine of Divine Mercy while enjoying free breakfast, WiFi, and parking. The 24-hour fitness centre and garden create a peaceful country getaway.
"Well-run and elegant property. "
United States
Steven
The price is ฿7,528
฿8,829 total
includes taxes & fees
5 Jan - 6 Jan
The Inn at Stockbridge
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

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

10/10 Excellent
"Pool was excellent ."
Robert 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Windsor

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ฿2,490 per night from 5 Jan to 6 Jan
฿2,490
฿2,782 total
5 Jan - 6 Jan
includes taxes & fees
7.4/10 Good! (827 reviews)

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 Hotel Downstreet, an Ascend Collection Hotel 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 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 Adams Theater, 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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