Deals on vacations and trips to Windsor

Save when you book Windsor package deals

Choose two or more items and save on your trip:

Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was $438, price is now $374 per person
$374
per person
Sep 8 - Sep 11
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a library, and dry cleaning are also offered.
Seacliff- Luxury Halifax Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Luxury Halifax Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

4.5 out of 5
Save 100% on your flight
Price was $4,901, price is now $3,779 per person
$3,779
per person
Aug 6 - Aug 10
found 2 days ago
Roundtrip flight included
New York (NYC) to Halifax (YHZ)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. A seasonal outdoor pool and laundry facilities are also provided.
HFX Airport Hotel

HFX Airport Hotel

2.5 out of 5
Price was $659, price is now $557 per person
$557
per person
Aug 9 - Aug 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and free perks like buffet breakfast and free self parking.
Future Inns Halifax

Future Inns Halifax

3 out of 5
Clayton Park West
Price was $1,023, price is now $885 per person
$885
per person
Sep 10 - Sep 14
found 17 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Halifax (YHZ)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a coffee shop, and a lobby fireplace are also offered.
Sandman Signature Dartmouth Hotel & Suites

Sandman Signature Dartmouth Hotel & Suites

3 out of 5
Price was $1,290, price is now $1,122 per person
$1,122
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Halifax (YHZ)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Top Windsor hotels deals

The August House

The August House

3.5 out of 5
494 King St Windsor NS
$156 nightly
The price is $183 total per night
$183 total
Jul 1 - Jul 2
Total with taxes and fees
This guesthouse features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden and a communal living room are also provided.
Gateway to Annapolis Valley | Windsor Studio Suite

Gateway to Annapolis Valley | Windsor Studio Suite

Windsor NS
$155 nightly
The price is $177 total per night
$177 total
Jul 28 - Jul 29
Total with taxes and fees
This apartment features laundry facilities.
Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor NS
Get rates
This apartment features laundry facilities.
Old Orchard Inn

Old Orchard Inn

4 out of 5
153 Greenwich Rd. South Wolfville Ridge NS
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $177 total per night
$177 total
Jul 7 - Jul 8
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this traditional hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Micro Boutique Living Wolfville

Micro Boutique Living Wolfville

3.5 out of 5
336 Main Street Wolfville NS
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $129 total per night
$129 total
Jul 13 - Jul 14
Total with taxes and fees
This apartment features free WiFi in public areas, laundry facilities, and self parking. A garden, a lobby fireplace, and a hair salon are also on offer.
Slumber Inn

Slumber Inn

3.5 out of 5
5534 Prospect Road New Minas NS
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $139 total per night
$139 total
Jul 7 - Jul 8
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. A garden, a computer station, and laundry facilities are also on offer.
Don't see what you're looking for?
See all available properties in Windsor
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

Haliburton House Museum

You can spend time studying the exhibits at Haliburton House Museum in Windsor. You can enjoy the wineries while in the area.

Haliburton House Museum

West Hants Historical Society

You can spend time browsing the exhibits at West Hants Historical Society in Windsor. You can enjoy the wineries while in the area.

West Hants Historical Society

Trecothic Creek and Windsor Railway

You can spend an afternoon studying the exhibits at Trecothic Creek and Windsor Railway during your travels in Windsor. You can enjoy the wineries while in the area.

Trecothic Creek and Windsor Railway

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity offers great package deals to Windsor, including flights and hotels, starting at just $374. With all the money you save, you could include some awesome tours or maybe also tack on a couple of extra nights to your getaway.
How long should my Windsor vacation be?
Your Windsor break can be as long as you want, but the majority of people stay roughly 4 nights. Eager to veer off the beaten path and uncover some lesser-known spots? Lock in a few extra nights and see another side of this place.
Where can I get the best vacation package deals for Windsor?
For the perfect Windsor package deal, you can't go past Travelocity. Take your pick from as many as 400 air carriers and 1,000,000 worldwide properties to create the ultimate adventure — it's really that easy.
Why should I purchase my Windsor vacation package with Travelocity?
The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you can relax knowing you're getting the best deal available.
Can I save money on my Windsor car rental if I combine it with hotels and flights?
Certainly. And our Windsor vacation packages are the ideal way to do it. In only a few clicks you can save money and time by bundling your bookings. Pick up the keys to your rental car and feel the freedom of the open road. Searching for things to do? Add some activities or experiences to your package and save on those too.
What is there to do in Windsor?
You'll notice a particular magic in the air as you wander through the streets of Windsor. Mermaid Theatre of Nova Scotia and Fort Edward National Historic Site are just two famous attractions that lure visitors to this fantastic city, so add them to your travel itinerary.
Where should I stay when visiting Windsor?
If you're after somewhere to lay your head, take a look at the The August House. It's the top pick for many travelers.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

A welcome sign at Cradle of Hockey, Long Pond, Windsor, Nova Scotia.

Explore More Ways to Travel with Travelocity