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Top Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (624)
"The perfect place "
The price is ₹13,414
₹16,952 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1009)
"Staff very nice and professional"
The price is ₹7,744
₹8,863 total
includes taxes & fees
5 Oct - 6 Oct
Quality Inn West Springfield

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Wonderful old inn; chock full of charm."
The price is ₹16,132
₹21,957 total
includes taxes & fees
22 Sept - 23 Sept
The Red Lion Inn

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2221)
"Very nice hotel with great rooms for affordable price"
The price is ₹10,829
₹12,581 total
includes taxes & fees
23 Sept - 24 Sept
D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1000)
"Excellent value Enjoyed breakfast- high quality and free Staff are well trained and very nice "
The price is ₹11,160
₹12,661 total
includes taxes & fees
5 Oct - 6 Oct
Tru by Hilton Chicopee Springfield

Courtyard by Marriott West Springfield

3.0 star property
9.2 out of 10, Wonderful, (512)
"Exceptionally satisfying stay in all aspects "
The price is ₹13,104
₹14,998 total
includes taxes & fees
25 Sept - 26 Sept
Courtyard by Marriott West Springfield

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

3.5 star property
9.0 out of 10, Wonderful, (719)
"Pleasant stay"
The price is ₹10,230
₹12,658 total
includes taxes & fees
25 Sept - 26 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1000)
"Great location!"
The price is ₹13,402
₹14,970 total
includes taxes & fees
14 Sept - 15 Sept
Hotel Downstreet, an Ascend Collection Hotel

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (716)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ₹14,155
₹15,811 total
includes taxes & fees
21 Sept - 22 Sept
Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ₹10,860
₹12,131 total
includes taxes & fees
24 Sept - 25 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
8.4 out of 10, Very good, (1000)
"Room was great,great breakfast, great place to stay with convenient access to highway"
The price is ₹10,036
₹11,140 total
includes taxes & fees
5 Oct - 6 Oct
Comfort Inn & Suites East Greenbush - Albany

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (497)
"Great hotel, staff and restaurant!"
The price is ₹18,280
₹20,419 total
includes taxes & fees
24 Sept - 25 Sept
The Williams Inn

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1010)
"Great place to stay"
The price is ₹11,929
₹13,325 total
includes taxes & fees
21 Sept - 22 Sept
Comfort Inn & Suites

Comfort Inn & Suites West Springfield

2.5 star property
7.6 out of 10, Good, (866)
"Good"
The price is ₹10,734
₹12,285 total
includes taxes & fees
5 Oct - 6 Oct
Comfort Inn & Suites West Springfield

Quality Inn Chicopee - Springfield

2.5 star property
6.4 out of 10, (770)
"Everything was great "
The price is ₹7,930
₹8,997 total
includes taxes & fees
26 Sept - 27 Sept
Quality Inn Chicopee - Springfield

Fairfield Inn & Suites Springfield Holyoke

2.5 star property
9.2 out of 10, Wonderful, (572)
"Great place in a great location."
The price is ₹11,896
₹13,287 total
includes taxes & fees
28 Sept - 29 Sept
Fairfield Inn & Suites Springfield Holyoke

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (36)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is ₹12,473
₹13,932 total
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Motel 6 Chicopee, MA - Springfield

2.0 star property
6.6 out of 10, (1002)
"It was a very nice place I would go again "
The price is ₹6,619
₹7,686 total
includes taxes & fees
11 Sept - 12 Sept
Motel 6 Chicopee, MA - Springfield

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (755)
"I would definitely stay here again!"
The price is ₹9,091
₹10,405 total
includes taxes & fees
7 Oct - 8 Oct
Candlewood Suites West Springfield by IHG

Hampton Inn West Springfield

2.5 star property
8.2 out of 10, Very good, (1000)
"Great stay"
The price is ₹10,411
₹11,915 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn West Springfield
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

Find out more about Windsor

Find out more about Windsor

Holiday Rentals in Windsor

Search for holiday rentals in Windsor on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its restaurants and shopping.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Mount Greylock State Reservation Visitor Center. Mount Greylock and Barrington Stage Company are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.