Windsor Vacation Packages 2026 from $818

Windsor flight + hotel vacation packages

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

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

$818

per person

Nov 11 - Nov 16

found 22 hours ago

Roundtrip flight included

Boston (BOS) 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.

Seasons Inn Halifax

Fairview

$894

per person

Nov 11 - Nov 16

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

The Lord Nelson Hotel & Suites

Downtown Halifax

$952

per person

Nov 11 - Nov 16

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a garden, and a hair salon are also offered.

Future Inns Halifax

Clayton Park West

$943

per person

Nov 11 - Nov 16

found 22 hours ago

Roundtrip flight included

Boston (BOS) 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.

Chateau Bedford, Trademark Collection by Wyndham

Birch Cove

$971

per person

Nov 11 - Nov 16

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Halifax (YHZ)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Top Windsor hotels deals

The August House

494 King St Windsor NS

$136 nightly

$159 total

Nov 1 - Nov 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.

Breakfast included

Parking included

Gateway to Annapolis Valley | Windsor Studio Suite

Windsor NS

$146 nightly

$167 total

Oct 6 - Oct 7

Total with taxes and fees

This apartment features laundry facilities.

Kitchen

Washer

Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor NS

$133 nightly

$151 total

Oct 5 - Oct 6

Total with taxes and fees

This apartment features laundry facilities.

Kitchen

Washer

Old Orchard Inn

153 Greenwich Rd. South Wolfville Ridge NS

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$171 total

Nov 2 - Nov 3

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.

Pool

Spa

Slumber Inn

5534 Prospect Road New Minas NS

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$130 total

Oct 19 - Oct 20

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.

Breakfast included

Pet friendly

Super 8 by Wyndham Windsor NS

63 Cole Drive Garlands Crossing NS

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$101 total

Nov 2 - Nov 3

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. There's an indoor pool on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Pool

Breakfast 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.

Stay near popular Windsor attractions

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.

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Frequently asked questions

How much are vacation packages to Windsor?

Travelocity offers great package deals to Windsor, including flights and hotels, starting at just $818. 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.