Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
SOHO Residences Champagne

SOHO Residences Champagne

4 out of 5
Centretown West
Price was $670, price is now $521 per person
$521
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ottawa (YOW)
A gym, self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, express check-in, and express check-out are also on offer.
Ottawa Marriott Hotel

Ottawa Marriott Hotel

4 out of 5
Downtown Ottawa
Price was $824, price is now $581 per person
$581
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ottawa (YOW)
This hotel features a restaurant, an indoor pool, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a garden are also offered.
Sheraton Ottawa Hotel

Sheraton Ottawa Hotel

4 out of 5
Downtown Ottawa
Price was $703, price is now $554 per person
$554
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ottawa (YOW)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a grocery/convenience store, and express check-out are also on offer.
Hotel V

Hotel V

3.5 out of 5
District des Promenades
Price was $953, price is now $766 per person
$766
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ottawa (YOW)
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Fairmont Chateau Laurier Gold Experience

Fairmont Chateau Laurier Gold Experience

5 out of 5
Downtown Ottawa
Price was $1,140, price is now $920 per person
$920
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Ottawa (YOW)
This hotel features an indoor pool, A 24-hour gym, and a restaurant. Unwind with a drink at the bar/lounge and enjoy perks like free continental breakfast and free WiFi. Valet parking, a business center, and a terrace are also offered.

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
$166 nightly
The price is $199 total per night
$199 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
A casino, 8 restaurants, and a 24-hour gym are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. Valet parking, a coffee shop, and a terrace are also offered.
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
$96 nightly
The price is $108 total per night
$108 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Express check-out is provided and the front desk is staffed around-the-clock.
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
Get rates
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, and free newspapers.
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
$79 nightly
The price is $89 total per night
$89 total
Dec 21 - Dec 22
Total with taxes and fees
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 facilities, and wedding services are also on offer.
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
$169 nightly
The price is $191 total per night
$191 total
Dec 23 - Dec 24
Total with taxes and fees
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 check-out are also on offer.
Spa
Parking included
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.

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

Mountain Memorial Community Park

Explore the great outdoors at Mountain Memorial Community Park, a lovely green space in North Dundas.

Mountain Memorial Community Park

Frequently asked questions

How much are vacation packages to Winchester?
Exciting adventures await in Winchester, with Travelocity vacation packages starting from just $521. 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 90 mi 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 20 mi northwest of central Winchester, is likely to be where you'll step off the plane. Your other options are Massena Intl. Airport (MSS) (25 mi away from central Winchester) and Ogdensburg Intl. Airport (OGS) (30 mi 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