Search for Cheap Deals on
Hotels in Winchester

Check Last Minute Winchester Hotel Deals

Tonight Jun 27 - Jun 28Next weekend Jul 3 - Jul 5

Choose from 47 Winchester Hotel Deals

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

4.5 out of 5
4837 Albion Road South Ottawa ON
  • 16 min drive from Calypso Water Park
Book a stay at this luxury resort in Ottawa. Enjoy free WiFi, free parking, and 8 restaurants. Popular attractions Rideau Carleton Raceway and Ernst & Young ...
9.2/10 Wonderful! (503 reviews)
"Great staff starting with check in Helpful. Comfortable beds and furniture. Very well maintained."

Reviewed on Jun 27, 2026

Hard Rock Hotel & Casino Ottawa
SureStay Hotel by Best Western Kemptville

SureStay Hotel by Best Western Kemptville

2.5 out of 5
4022 County Road 43 North Grenville ON
  • 53 min drive from Calypso Water Park
Book a stay at this business-friendly hotel in Kemptville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
8/10 Very Good! (577 reviews)
"Could use a better breakfast. Just toast, yogurt and"

Reviewed on Jun 22, 2026

SureStay Hotel by Best Western Kemptville
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
  • 1 hour drive from Calypso Water Park
Stay at this hotel in South Dundas. Enjoy free parking, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.4/10 Very Good! (479 reviews)
"We were allowed to leave our bikes in the meeting room next to check in which was helpful. The rambling layout meant a long walk to our room. The decor is aging and fixtures dated but the room and halls were clean. Breakfast was not included in the rate making this stay more expensive than other, ..."

Reviewed on Jun 13, 2026

McIntosh Country Inn & Conference Centre in Canada
Kemptville Suites

Kemptville Suites

4 out of 5
103 Clothier St. East North Grenville ON
  • 56 min drive from Calypso Water Park
Stay at this hotel in Kemptville. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions North Grenville Public Library - Kemptville Branch ...
9.6/10 Exceptional! (300 reviews)
"Yes the AC was great. Would be nice to be able to open a window to get fresh air. The amenities such as robes and shampoo and teas and coffee were very good quality. Great response when i needed to call about the door code. Snacks heslthier than duritos would be nice but over all the place was great. ..."

Reviewed on Jun 18, 2026

Kemptville Suites
Bed & Stay

Bed & Stay

2 out of 5
659 Parkview Ter Russell ON
  • 10 min drive from Calypso Water Park
Stay at this guesthouse in Russell. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Keith M. Boyd Park and Parc de la Piscine ...
9.2/10 Wonderful! (63 reviews)
"Lovely home, clean, spacious, bright, great location for us. Convenient. Staff were responsive to questions. Our room and ensuite was spacious. Parking was not an issue. Nice neighbourhood with a walking path around the water reservoir."

Reviewed on Apr 22, 2026

Bed & Stay
Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

3 out of 5
11952 County Road 43 North Dundas ON
  • 40 min drive from Calypso Water Park
Stay at this B&B in North Dundas. Enjoy free breakfast, free WiFi, and free parking.
9.6/10 Exceptional! (121 reviews)
"It was a welcomed stay as both my husband and I really needed a night away to relax. The property is clean enough and I wouldn't be afraid to stay again, but let's say my house after a clean on Saturday is much cleaner. The owner wasn't going out of her way to accommodate but she was kind. The breakfast ..."

Reviewed on Jun 20, 2026

Terrace Green Bed & Breakfast
Doran Bay Resort

Doran Bay Resort

2.5 out of 5
11128 County Road 2 South Dundas ON
  • 1 hour drive from Calypso Water Park
Book a stay at this beach cottage in South Dundas. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Iroquois Golf Club and Iroquois Beach ...
7.8/10 Good! (24 reviews)
"Beautiful nature before cottage door. Kind staff."

Reviewed on Jun 22, 2026

Doran Bay Resort
Cedar Drive Inn

Cedar Drive Inn

3 out of 5
14990 Concession 10-11 Road North Stormont ON
  • 15 min drive from Calypso Water Park
Stay at this guesthouse in North Stormont. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
Cedar Drive Inn
KC's Country Inn

KC's Country Inn

2.5 out of 5
984 Burton Rd. Russell ON
  • 6 min drive from Calypso Water Park
Stay at this motel in Russell. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Alcide ...
7.6/10 Good! (333 reviews)
"😊"

Reviewed on Jun 23, 2026

KC's Country Inn
Strathmere Country Retreat

Strathmere Country Retreat

2 out of 5
1980 Phelan Rd W Ottawa ON
  • 36 min drive from Calypso Water Park
Book a stay at this spa hotel in Ottawa. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Manderley on the Green and Watson's Mill are ...
2/10 (1 review)
"The reservation did not exist when i arrived Either Expedia or strathmere messed up badly"

Reviewed on Feb 15, 2026

Strathmere Country Retreat
Enduring Heart Bed and Breakfast Inc.

Enduring Heart Bed and Breakfast Inc.

3.5 out of 5
1590 County Rd 18 North Grenville ON
  • 1 hour drive from Calypso Water Park
Stay at this B&B in North Grenville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Westerra Park and Riverside Park are located ...
Enduring Heart Bed and Breakfast Inc.
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.

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 47 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 $87. 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 great 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 unlock great deals on 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 $87.

How many hotels are there in Winchester?

With over 47 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 $87.

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 unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.