Book Cheap Hotels in Winchester

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Check prices in Winchester for tonight, Dec 18 - Dec 19
Dec 18 - Dec 19
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Dec 19 - Dec 20
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Check prices in Winchester for this weekend, Dec 19 - Dec 21
Dec 19 - Dec 21
Next weekend
Check prices in Winchester for next weekend, Dec 26 - Dec 28
Dec 26 - Dec 28

Most frequently booked Winchester hotels

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

Winchester ON
0.25 km from city centre
Get rates
Stay at this vacation home in North Dundas. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces.
Kitchen
Pet-friendly
Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

4 out of 5
4837 Albion Road South Ottawa ON
Free cancellation
Reserve now, pay when you stay
29.97 km from city centre
The price is CA $229 per night
CA $229
CA $274 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this resort in Ottawa. Enjoy free WiFi, free parking, and 8 restaurants. Popular attractions Rideau Carleton Raceway and Ernst & Young Centre are located nearby.
Pet-friendly
Parking included
SureStay Hotel by Best Western Kemptville

SureStay Hotel by Best Western Kemptville

2.5 out of 5
4022 County Road 43 North Grenville ON
Free cancellation
Reserve now, pay when you stay
21.85 km from city centre
The price is CA $133 per night
CA $133
CA $150 total
Dec 20 - Dec 21
includes taxes & fees
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 and the clean rooms in our reviews. Popular attractions Kemptville Colonnade and South Branch Cove Park are located nearby.
Breakfast included
Pet-friendly
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
Free cancellation
Reserve now, pay when you stay
25.18 km from city centre
The price is CA $169 per night
CA $169
CA $191 total
Jan 1 - Jan 2, 2026
includes taxes & fees
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 Upper Canada Playhouse and Dupont Provincial Park are located nearby.
Pool
Hot tub
KC's Country Inn

KC's Country Inn

2.5 out of 5
984 Burton Rd. Russell ON
Free cancellation
Reserve now, pay when you stay
26.56 km from city centre
The price is CA $109 per night
CA $109
CA $123 total
Dec 21 - Dec 22
includes taxes & fees
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 Trudeau Park and Stanley Park are located nearby.
Pet-friendly
Parking included
Kemptville Suites

Kemptville Suites

4 out of 5
103 Clothier St. East North Grenville ON
Free cancellation
Reserve now, pay when you stay
24.81 km from city centre
The price is CA $233 per night
CA $233
CA $263 total
Dec 23 - Dec 24
includes taxes & fees
Stay at this hotel in Kemptville. Enjoy free WiFi, free parking, and onsite spa services. Popular attractions North Grenville Public Library - Kemptville Branch and North Grenville Archives are located nearby.
Spa
Parking included
Bed & Stay

Bed & Stay

2 out of 5
659 Parkview Ter Russell ON
Free cancellation
Reserve now, pay when you stay
19.42 km from city centre
The price is CA $86 per night
CA $86
CA $122 total
Dec 19 - Dec 20
includes taxes & fees
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 are located nearby.
Parking included
Free WiFi
Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

3 out of 5
11952 County Road 43 North Dundas ON
Free cancellation
Reserve now, pay when you stay
2.27 km from city centre
The price is CA $125 per night
CA $125
CA $141 total
Jan 3 - Jan 4, 2026
includes taxes & fees
Stay at this B&B in North Dundas. Enjoy free breakfast, free WiFi, and free parking.
Breakfast included
Spa
Cedar Drive Inn

Cedar Drive Inn

3 out of 5
14990 Concession 10-11 Road North Stormont ON
21.23 km from city centre
The price is CA $135 per night
CA $135
CA $153 total
Dec 19 - Dec 20
includes taxes & fees
Stay at this inn in North Stormont. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Casselview Golf and Country Club and Domaine du Cervin are located nearby.
Parking included
Free WiFi
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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.

Winchester hotels essential information

Accommodation
42 hotels
Lowest Price
CA $122
Highest Price
CA $274
Popular hotels
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa, Hard Rock Hotel & Casino Ottawa, SureStay Hotel by Best Western Kemptville, McIntosh Country Inn & Conference Centre in Canada, KC's Country Inn, Kemptville Suites, Bed & Stay, Terrace Green Bed & Breakfast, Cedar Drive Inn

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
Terrace Green Bed & Breakfast is the perfect choice for families heading to Winchester. With helpful amenities like complimentary breakfast, this kid-friendly option will make everyone in your group feel right at home.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is CA $122 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 42 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during May, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as December, January and February.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Super place and excellent food"
A verified traveller stayed at Hard Rock Hotel & Casino Ottawa
Hard Rock Hotel & Casino Ottawa

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