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Top hotels and accommodation in Windsor

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, (1006)
"Good Location"
The price is NZ$214
includes taxes & fees
7 Aug - 8 Aug
Red Roof Inn PLUS+ South Deerfield – Amherst
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (105)
"Great Place to stay in Small town"
The price is NZ$227
includes taxes & fees
30 July - 31 July
Blooming Inn
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is NZ$215
includes taxes & fees
27 July - 28 July
Becket Motel
Blue Vista Motor Lodge
Single Room

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (176)
"Lovely stay!"
The price is NZ$423
includes taxes & fees
4 Aug - 5 Aug
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (132)
"Stayed only one night Very cosy, quiet place "
The price is NZ$347
includes taxes & fees
27 July - 28 July
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
Romantic Room, 1 King Bed (Room 4)

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (5)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is NZ$333
includes taxes & fees
3 Aug - 4 Aug
The Revival House
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, (1006)
"Great place"
The price is NZ$314
includes taxes & fees
27 July - 28 July
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (395)
"Beautiful and peaceful property. Perfect for our last minute mother daughter get away. The staff was friendly and helpful. "
The price is NZ$434
includes taxes & fees
18 Aug - 19 Aug
The Porches Inn at Mass MoCA
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is NZ$413
includes taxes & fees
4 Aug - 5 Aug
Harbour House Inn
Pilgrim Inn
Lobby

Pilgrim Inn

2.5 star property
5.8 out of 10, (310)
"Great location but no staff at check-in or checkout!"
The price is NZ$133
includes taxes & fees
10 Aug - 11 Aug
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1005)
"The complimentary breakfast was amazing!"
The price is NZ$250
includes taxes & fees
6 Aug - 7 Aug
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (393)
"No frills but it was a great stay!"
The price is NZ$199
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (751)
"Close to our target event a plus"
The price is NZ$131
includes taxes & fees
6 Aug - 7 Aug
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (614)
"It was a clean, well-run, low cost option. "
The price is NZ$118
includes taxes & fees
6 Aug - 7 Aug
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
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, (1004)
"Beautiful location!"
The price is NZ$360
includes taxes & fees
30 July - 31 July
The Black Swan Lee - Lenox, Ascend Hotel Collection
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, (680)
"Had a great time"
The price is NZ$279
includes taxes & fees
30 July - 31 July
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is NZ$328
includes taxes & fees
27 July - 28 July
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NZ$362
includes taxes & fees
27 July - 28 July
Hilton Garden Inn Lenox Pittsfield
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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Learn more about Windsor

Explore Windsor: its dining and more!

See all hotels in Windsor

Top Windsor Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"The hotel was very unique as there was art spaces in the lobby. Liked that the room had lvp flooring. "
stephen 2-night trip
Posted 17 hours ago
Hotel Downstreet, Ascend Hotel Collection

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 Red Roof Inn PLUS+ South Deerfield – Amherst and The Williams Inn. See all available top hotels, or vacation rentals in Windsor.

What are some of the best holiday rentals that Windsor has to offer?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Windsor offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly. See all 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 Bas Ridge Golf Course, 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.