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Winchester flight + hotel packages

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Cartier Place Suite Hotel

Cartier Place Suite Hotel

3 out of 5
Downtown Ottawa
Price was CA $746, price is now CA $557 per person
CA $557
per person
Feb 18 - Feb 21
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Ottawa (YOW)
Stay at this aparthotel in Ottawa. Enjoy free WiFi, room service, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Byward Market Square and Rideau Canal are located nearby.
Fairmont Chateau Laurier Gold Experience

Fairmont Chateau Laurier Gold Experience

5 out of 5
Downtown Ottawa
Price was CA $1,458, price is now CA $1,130 per person
CA $1,130
per person
Mar 5 - Mar 8
found 3 hours ago
Roundtrip flight included
Halifax (YHZ) to Ottawa (YOW)
Book a stay at this luxury hotel in Ottawa. Enjoy free breakfast, free WiFi, and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Byward Market Square and Rideau Canal are located nearby.
Ottawa Marriott Hotel

Ottawa Marriott Hotel

4 out of 5
Downtown Ottawa
Price was CA $1,044, price is now CA $819 per person
CA $819
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Ottawa (YOW)
Stay at this hotel in Ottawa. Enjoy breakfast (surcharge), valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Byward Market Square and Rideau Canal are located nearby.
Duvernay Studios and Suites

Duvernay Studios and Suites

2.5 out of 5
Hull
Price was CA $720, price is now CA $586 per person
CA $586
per person
Mar 16 - Mar 20
found 24 hours ago
Roundtrip flight included
Halifax (YHZ) to Ottawa (YOW)
Stay at this apartment in Gatineau. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Byward Market Square and Casino du Lac Leamy are located nearby.
Hotel V

Hotel V

3.5 out of 5
District des Promenades
Price was CA $983, price is now CA $807 per person
CA $807
per person
Mar 5 - Mar 8
found 3 hours ago
Roundtrip flight included
Halifax (YHZ) to Ottawa (YOW)
Book a stay at this spa hotel in Gatineau. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Casino du Lac Leamy and Byward Market Square are located nearby.

Top Winchester hotels deals

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

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

Winchester ON
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
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
The price is CA $133 per night
CA $133
CA $150 total
Dec 31 - Jan 1, 2026
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
The price is CA $159 per night
CA $159
CA $180 total
Dec 31 - Jan 1, 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
The price is CA $109 per night
CA $109
CA $123 total
Dec 30 - Dec 31
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.
Kemptville Suites

Kemptville Suites

4 out of 5
103 Clothier St. East North Grenville ON
Free cancellation
Reserve now, pay when you stay
The price is CA $233 per night
CA $233
CA $263 total
Jan 12 - Jan 13, 2026
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
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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.

Popular places to visit

Sandy Mountain Golf Course

Enjoy a round of golf in North Dundas at Sandy Mountain Golf Course.

Sandy Mountain Golf Course

Smokie Ridge Vineyard

You can enjoy a tasting or tour at Smokie Ridge Vineyard during your travels to North Dundas.

Smokie Ridge Vineyard

Domaine du Cervin

You can enjoy a tasting or tour at Domaine du Cervin during your travels to North Dundas. Make some time to visit the spas while you're in the area.

Domaine du Cervin

Winchester Vacations

If you were away the day your geography teacher taught the class where Winchester is located, don't worry. With the following useful information, you'll be able to find it in a flash!

You can find it 25 miles (40 kilometers) away from Massena and 30 miles (48 kilometers) away from Ogdensburg.

Hotels in Winchester

You'll need to act quickly if you'd like to stay close to Winchester. The Terrace Green Bed & Breakfast is the only property in the vicinity of of the center.

Places to visit in Winchester

Enjoy the rich scent of a glass of wine? Stop at Domaine du Cervin and find out the expert techniques involved in transforming grapes into one of the world's most delicious beverages. When you've had your fill of sightseeing, give cross-country skiing a go. It's a fun and popular way to enjoy a different side of the wider region.

Where do you fly into for Winchester?

The buzz of roaming a totally new destination never gets old. Once you've safely touched down at Macdonald-Cartier International Airport (YOW), the middle of Winchester will be only 20 miles (32 kilometers) to the southeast from here.

Frequently asked questions

How much are vacation packages to Winchester?
Exciting adventures await in Winchester, with Travelocity vacation packages starting from just CA $557. Providing both hotels and flights, these terrific deals are an easy way to see every corner of the globe.
Where can I get the best vacation package deals for Winchester?
You'll come across a terrific range of Winchester package deals on Travelocity. With 400 airlines and 1,000,000 properties around the globe, piecing together your dream getaway won't take long.
Why should I book my Winchester vacation bundle with Travelocity?
Incredible savings, countless thrilling destinations and a team of customer service experts available 24/7 — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always get the best possible deal with Travelocity.
Can I save money on my Winchester car rental if I combine it with hotels and flights?
Combining your hotel, flight and car into a Winchester vacation package is a great way to score an amazing deal. Plus, having your own wheels gives you the freedom to make your way to all the landmarks you want to see. Sitting 145 kilometers away from Winchester, Notre Dame Basilica is one place that should be on your itinerary. Turn up the tunes and make a day trip of it.
Which airport is best for Winchester?
Macdonald-Cartier Intl. Airport (YOW), around 32 kilometers northwest of central Winchester, is likely to be where you'll step off the plane. Your other options are Massena Intl. Airport (MSS) (40 kilometers away from central Winchester) and Ogdensburg Intl. Airport (OGS) (48 kilometers away from central Winchester).
Where should I stay when visiting Winchester?
Many people stay at the Terrace Green Bed And Breakfast. It's an excellent base for your Winchester getaway.

Photos of local treasures

Browse Winchester vacation photos for more inspiration