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Compare 56 Cottages in Windsor with updated reviews, rates, and availability.

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2361)
"Safe "
The price is AED 391
AED 454 total
includes taxes & fees
9 Mar - 10 Mar
D. Hotel Suites & Spa

Life House Berkshires

3.5 star property
9.2 out of 10, Wonderful, (513)
"The restaurant and lounge area is so inviting, and staff is all around excellent."
The price is AED 355
AED 397 total
includes taxes & fees
19 Mar - 20 Mar
Life House Berkshires

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (426)
"Tradition ski inn with great common areas. "
The price is AED 450
AED 546 total
includes taxes & fees
9 Mar - 10 Mar
Mountaineer Inn

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1007)
"This was a very nice little getaway from everyday life. The room was nice and roomy and we loved the fireplace. "
The price is AED 293
AED 328 total
includes taxes & fees
17 Mar - 18 Mar
The Yankee, Trademark Collection by Wyndham

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (419)
"Very nice boutique hotel in a wonderful college town. Winter season caused Wi-Fi, electricity and staff shortages. Overall nice stay. "
The price is AED 746
AED 833 total
includes taxes & fees
9 Mar - 10 Mar
The Williams Inn

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1008)
"Great service and very clean."
The price is AED 451
AED 504 total
includes taxes & fees
1 Apr - 2 Apr
Comfort Inn & Suites

Mount Snow Grand Summit Resort

3.0 star property
8.6 out of 10, Excellent, (186)
"Outdoor pool was great !"
The price is AED 933
AED 1,117 total
includes taxes & fees
1 Apr - 2 Apr
Mount Snow Grand Summit Resort

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1004)
"Exactly what I needed after being stressed out from work for the past few months. The laundry service may have out of service, but I dont care. All I needed was to decompress and this hotel helped me do exactly that. Thank you for a lovely weekend and I'll definitely come back when I get the chance.😊"
The price is AED 434
AED 485 total
includes taxes & fees
20 Mar - 21 Mar
Hotel Downstreet, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Some aspects were great, some not. The hotel restruant is an Indian cuisine which we do not like. The room we stayed in has wall and floor structural problems. There was also a camera pin hole in the ceiling over the tub I stuffed a tissue into. It was noisy between 10 to 11 pm as a group of loud drunks were walking down the hall."
The price is AED 359
AED 401 total
includes taxes & fees
13 Mar - 14 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection

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

3.5 star property
9.0 out of 10, Wonderful, (606)
"It is convenient for families with little ones during the off-season to have fun with the pool-activities-arcade and movie theatre on site. It is an easy drive from areas of MA-NY and CT to make it a convenient family weekend get away-rooms are getting dated and could use some sprucing and updating but are overall clean "
The price is AED 437
AED 539 total
includes taxes & fees
9 Mar - 10 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1005)
"Howard Johnson's is a reliable place to stay when I visit Amherst. It's clean, comfortable, affordable and conveniently located. Nothing posh or fancy about it, but it serves its purpose well. Mini fridge in room is a nice plus. Would be nice if they had in-room microwaves."
The price is AED 365
AED 408 total
includes taxes & fees
12 Mar - 13 Mar
Howard Johnson by Wyndham Amherst Hadley

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (439)
"Great room. Comfortable. Wished we stayed longer! Will definitely recommend to friends and family. "
The price is AED 437
AED 562 total
includes taxes & fees
16 Mar - 17 Mar
Berkshire Mountain Lodge

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (745)
"Great location for my needs. Quiet and clean price was right as well. "
The price is AED 382
AED 427 total
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Homewood Suites by Hilton Holyoke-Springfield/North

3.0 star property
9.0 out of 10, Wonderful, (964)
"Very nice and clean "
The price is AED 475
AED 530 total
includes taxes & fees
13 Mar - 14 Mar
Homewood Suites by Hilton Holyoke-Springfield/North

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1005)
"Good"
The price is AED 311
AED 356 total
includes taxes & fees
12 Mar - 13 Mar
Red Roof Inn PLUS+ West Springfield

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Love the history and ambiance. Service excellent. Restaurant dinner just fair. Clean rooms. Guests should not have to pay for music in the bar. Parking good. Very quiet. "
The price is AED 511
AED 734 total
includes taxes & fees
31 Mar - 1 Apr
The Red Lion Inn

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1010)
"Great place to stay has plenty of places around to shop and eat would stay again. Thank you for the experience "
The price is AED 356
AED 404 total
includes taxes & fees
23 Mar - 24 Mar
Tru by Hilton Chicopee Springfield

Best Western Bennington

2.5 star property
7.8 out of 10, Good, (822)
"I can always count on Steve at the front desk for a great experience at the Bennington BW."
The price is AED 389
AED 423 total
includes taxes & fees
13 Mar - 14 Mar
Best Western Bennington

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very Good, (657)
"Our stay was great at the Candlewood Suites. All of the staff were wonderful and very accommodating. The kids loved the pool and the snack room. Also, the one bedroom room was great for families and the bed was very comfortable. The location was great to go to the basketball hall of fame and MGM. It was also only 50 minutes to skiing. "
The price is AED 323
AED 370 total
includes taxes & fees
14 Mar - 15 Mar
Candlewood Suites West Springfield by IHG

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (621)
"The place is attractive and comfortable. It's in a location convenient for restaurants and Smith College and they offer a good selection for breakfast."
The price is AED 474
AED 529 total
includes taxes & fees
10 Mar - 11 Mar
The Ellery
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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Other property types in Windsor

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1784)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"
The price is AED 400
AED 476 total
includes taxes & fees
10 Mar - 11 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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.

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between and per night. These properties offer a chance to soak up nature’s beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Windsor with Expedia?
Expedia has some wonderful cottages in Windsor, so start packing your bags for a memorable vacation on nature’s doorstep. If you have a budget in mind, select how much you’d like to spend and the star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a pool. We’ll help you find the right digs whatever your plans or bank balance.
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