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.
Arc The Hotel

Arc The Hotel

4 out of 5
Downtown Ottawa
Price was $845, price is now $662 per person
$662
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Ottawa (YOW)
A restaurant and a bar/lounge are featured at this hotel. Self parking, dry cleaning, and luggage storage are also offered.
Sheraton Ottawa Hotel

Sheraton Ottawa Hotel

4 out of 5
Downtown Ottawa
Price was $898, price is now $710 per person
$710
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
SOHO Residences Lisgar

SOHO Residences Lisgar

4 out of 5
Downtown Ottawa
Price was $855, price is now $678 per person
$678
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Ottawa (YOW)
This aparthotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a terrace, and a garden are also offered.
SOHO Residences Champagne

SOHO Residences Champagne

4 out of 5
Centretown West
Price was $855, price is now $678 per person
$678
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
reStays Ottawa

reStays Ottawa

4 out of 5
Downtown Ottawa
Price was $1,082, price is now $889 per person
$889
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Ottawa (YOW)
A restaurant and a gym are featured at this hotel. Enjoy the sauna and perks like free WiFi. Self parking, a terrace, and express check-out are also offered.

Top Winchester hotels deals

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
$82 nightly
The price is $93 total per night
$93 total
Oct 12 - Oct 13
Total with taxes and fees
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 garden, and a picnic area are also on offer.
Breakfast included
Spa
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

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

$170 nightly
The price is $192 total per night
$192 total
Oct 26 - Oct 27
Total with taxes and fees
Stay at this vacation home in North Dundas. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces.
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
$143 nightly
The price is $169 total per night
$169 total
Oct 7 - Oct 8
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
Microtel by Wyndham Casselman

Microtel by Wyndham Casselman

3 out of 5
17 Rue Industriel, Casselman, ON
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $119 total per night
$119 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-in, and conference space. There's a gym on site, and laundry facilities and concierge services are also offered.
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
$102 nightly
The price is $115 total per night
$115 total
Oct 26 - Oct 27
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.
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.
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

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

Sandy Mountain Golf Course

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

Sandy Mountain Golf Course

Frequently asked questions

How much are vacation packages to Winchester?
Exciting adventures await in Winchester, with Travelocity vacation packages starting from just $662. 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