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Hotels in Winchester

Last Minute Hot Rate® Hotel Deals in Winchester

We Hide Hotel Names So You Can Find 4-Star Hotels At 2-Star Prices. Choose the Location, Star Rating & Amenities. Let Hotwire Find You the Best Deal. Book Today!

Choose from 17 Winchester Hotel Deals

Terrace Green Bed & Breakfast
Terrace Green Bed & Breakfast
3 out of 5
11952 County Road 43, North Dundas, ON, K0C2K0
  • 35 min drive from Upper Canada Village
The price is $74 per night from May 27 to May 28
Stay at this 3-star B&B in North Dundas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the comfy beds in our reviews. ...
Terrace Green Bed & Breakfast
Microtel by Wyndham Casselman
Microtel by Wyndham Casselman
3 out of 5
17 Rue Industriel, Casselman, ON, K0A 1M0
  • 1 hour drive from Upper Canada Village
The price is $129 per night from May 27 to May 28
Stay at this 3-star business-friendly hotel in Casselman. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Microtel by Wyndham Casselman
McIntosh Country Inn & Conference Centre in Canada
McIntosh Country Inn & Conference Centre in Canada
3.5 out of 5
12495 Highway 2 East, South Dundas, ON, K0C 1X0
  • 12 min drive from Upper Canada Village
The price is $140 per night from May 25 to May 26
Stay at this 3.5-star business-friendly hotel in South Dundas. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful ...
McIntosh Country Inn & Conference Centre in Canada
Cedar Drive Inn
Cedar Drive Inn
3 out of 5
14990 Concession 10-11 Road, North Stormont, ON, K0A 1R0
  • 47 min drive from Upper Canada Village
The price is $90 per night from May 25 to May 26
Stay at this 3-star business-friendly B&B in North Stormont. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast and the helpful ...
Cedar Drive Inn
SureStay Hotel by Best Western Kemptville
SureStay Hotel by Best Western Kemptville
2.5 out of 5
4022 County Road 43, North Grenville, ON, K0G 1J0
  • 50 min drive from Upper Canada Village
The price is $109 per night from May 29 to May 30
Stay at this business-friendly hotel in Kemptville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy beds ...
SureStay Hotel by Best Western Kemptville
KC's Country Inn
KC's Country Inn
2.5 out of 5
984 Burton Rd., Russell, ON, K0A 3H0
  • 1 hour drive from Upper Canada Village
The price is $78 per night from May 29 to May 30
Stay at this motel in Russell. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Discover ...
KC's Country Inn
Kemptville Suites
Kemptville Suites
4 out of 5
103 Clothier St. East, North Grenville, ON, K0G 1J0
  • 53 min drive from Upper Canada Village
The price is $260 per night from May 29 to May 30
Stay at this 4-star hotel in Kemptville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the spacious rooms ...
Kemptville Suites
Enduring Heart Bed and Breakfast Inc.
Enduring Heart Bed and Breakfast Inc.
3.5 out of 5
1590 County Rd 18, North Grenville, ON, K0G 1S0
  • 58 min drive from Upper Canada Village
Stay at this 3.5-star B&B in North Grenville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Rideau Canal and Rideau Glen Golf Club are ...
Enduring Heart Bed and Breakfast Inc.
Abbott Road Suites
Abbott Road Suites
3.5 out of 5
2204 Abbott Road, North Grenville, ON, K0G 1J0
  • 55 min drive from Upper Canada Village
Stay at this 3.5-star golf aparthotel in Kemptville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the comfy beds in our reviews. ...
Abbott Road Suites
Doran Bay Resort
Doran Bay Resort
2.5 out of 5
11128 County Road 2, South Dundas, ON, K0E 1K0
  • 26 min drive from Upper Canada Village
Stay at this beach cottage in South Dundas. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the family amenities in our reviews. ...
Doran Bay 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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in Winchester

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Winchester hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Winchester.

Choosing the right hotel in Ontario has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Winchester’s 17 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $74. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Winchester hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Winchester. No matter your reason for visiting Winchester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Winchester hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Winchester for as low as $74.

How many hotels are there in Winchester?

With over 17 hotels in Winchester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $74.

How to find cheap car rentals in Winchester?

Finding a cheap car rental deal in Winchester is as easy as scoring cheap hotels in Winchester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Winchester now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Winchester right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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