Book Hotels in Winchester

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top hotels

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

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

Winchester
Stay at this vacation home in North Dundas. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces.
Nice place
"How is very well designed and equipped, full of nice details. Location cannot be better. Communication has been great and listing accurate. Highly recommended!"

Reviewed on May 17, 2025

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

3 out of 5
11952 County Road 43, North Dundas, ON
Fully refundableReserve now, pay when you stay
This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free full breakfast each morning. A terrace, a ...
"Well done property - clean and pleasant place"

Reviewed on Jun 19, 2025

Terrace Green Bed & Breakfast
Kemptville Suites

Kemptville Suites

4 out of 5
103 Clothier St. East, North Grenville, ON
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A hair salon, express check-in, and express ...
"Beautiful renovation of historic building"

Reviewed on Jun 23, 2025

Kemptville Suites
659 Parkview Ter

659 Parkview Ter

2 out of 5
659 Parkview Ter, Russell, ON
This guesthouse includes a fireplace in the lobby and laundry facilities. Take advantage of the free self parking.
"Great place"

Reviewed on Jun 20, 2025

659 Parkview Ter
Cedar Drive Inn

Cedar Drive Inn

3 out of 5
14990 Concession 10-11 Road, North Stormont, ON
Fully refundable
This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and luggage storage are also on offer.
"Nice clean and tidy place! Felt welcomed from the start. Definitely will stay again if in the area."

Reviewed on May 29, 2025

Cedar Drive Inn
Microtel by Wyndham Casselman

Microtel by Wyndham Casselman

3 out of 5
17 Rue Industriel, Casselman, ON
Fully refundableReserve now, pay when you stay
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of ...
"Great Hotel"

Reviewed on Jun 20, 2025

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
Fully refundableReserve now, pay when you stay
This hotel features 2 restaurants, 2 hot tubs, and a gym. Enjoy the seasonal outdoor pool and perks like free self parking. You'll appreciate the sauna, bar/lounge, ...
"The attached restaurant was excellent. Room was clean and comfortable. Customer service was outstanding... every single employee that we spoke to were awesome. We'll be back!!"

Reviewed on Jun 22, 2025

McIntosh Country Inn & Conference Centre in Canada
SureStay Hotel by Best Western Kemptville

SureStay Hotel by Best Western Kemptville

2.5 out of 5
4022 County Road 43, North Grenville, ON
Fully refundableReserve now, pay when you stay
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
Updated Rooms
"Older hotel building but with recent upgrades. Loved that the floors were LVP instead of carpet. Rooms looked like they had recent update with new fixtures. Front desk was not manned when we checked in, shortly after 10pm. Breakfast was mediocre with mostly packaged food choices."

Reviewed on Jun 19, 2025

SureStay Hotel by Best Western Kemptville
KC's Country Inn

KC's Country Inn

2.5 out of 5
984 Burton Rd., Russell, ON
A restaurant and a bar/lounge are featured at this motel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, laundry ...
Clean, comfortable, convenient.
"Clean, comfortable bed, nicely redone bathroom. Looking for a place to sleep, it was good for me. Adjacent food truck and convenience store was helpful. Did not stay to sample the half-price breakfast."

Reviewed on May 15, 2025

KC's Country Inn
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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 Hotel & Travel Guide\n

Are you dreaming about an adventure in Winchester? You will want to secure accommodations in advance, as there is only 1 room within an easy driving distance of the center of Winchester.

A handy option amongst only a few Travelocity-listed rooms within a short walk of the sights of central Winchester, is the Terrace Green Bed & Breakfast.

The Knights Inn Kemptville is about 14 miles (22 kilometers) outside the city center of Winchester. Another accommodation option is the KC's Country Inn, which can be found 17 miles (27 kilometers) away. Some other accommodation options here include the Cedar Drive Bed and Breakfast and the Country View Manor.

If time is on your side, why not visit the other attractions located in Ottawa - Southeastern Ontario while you are in this area? Ottawa - Southeastern Ontario boasts forests and rivers, and other commonly visited tourist places of interest include old towns. Common pastimes in this region of Canada include cross-country skiing.

Ottawa is 30 miles (46 kilometers) northwest of Winchester and features Parliament Hill and National Gallery of Canada. Travelocity-listed Ottawa places to base yourself include the Hilton Lac-Leamy and Fairmont Chateau Laurier. Alternatively, you could consider staying at Cornwall, 30 miles (48 kilometers) to the east of Winchester, where you can choose from the Best Western Parkway Inn & Conference Centre and Ramada Cornwall. Regardless of whether you're passing through or spending a few nights in Cornwall, make sure you explore the Cornwall Community Museum and Archie's Family Golf Centre.

Consider spending an afternoon enjoying thrills and spills with Ottawa - Southeastern Ontario's sports enthusiasts at a community sporting fixture. You'll find Canadian Tire Centre 30 miles (50 kilometers) to the northwest of Winchester. Find a Travelocity-listed hotel nearby to the action at the Holiday Inn Hotel & Suites Ottawa Kanata or the Fairfield Inn & Suites by Marriott Ottawa Kanata.

Macdonald-Cartier International Airport is a major entry point for those accessing Winchester. It's located 20 miles (36 kilometers) from the town center. For modern travelers who plan to find a Travelocity-listed base nearby, book the Days Inn Ottawa Airport or Holiday Inn Express Hotel & Suites Ottawa Airport.

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 . 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 50 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