Collingwood Vacations

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Collingwood Flight + Hotel packages

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Cottage on Caledonia Bed & Breakfast

Cottage on Caledonia Bed & Breakfast

$1,081
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Toronto (YYZ)
Stay at this B&B in Stratford. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Festival Theatre and Shakespearean Gardens are located nearby.
The Bed%Breakfast at 61 Caledonia in Stratford is a very cute property. The rooms and the whole house were very neat and tidy. The breakfast was very rich and the owners Sue and Ted were very friendly and lovely people. We talked about almost everything. Of course, we compared notes about the Stratford Festivals' current and some of the previous years' plays and the musicals. If I did not have to attend a presentation at Tom Patterson theater, I was probably going to continue our conversation and taste everything which was on the breakfast table. I strongly recommend this property. Mig

Reviewed on Aug 30, 2026

Ambassador's Inn Next Door

Ambassador's Inn Next Door

$1,342
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Toronto (YYZ)
Stay at this B&B in Stratford. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Festival Theatre and Tom Patterson Theatre are located nearby.
Great location for walking to all the theaters.

Reviewed on Aug 31, 2026

Clonmel Castle

Clonmel Castle

$1,328
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Toronto (YYZ)
Book a stay at this boutique B&B in Norfolk County. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Lynn River Falls and Powell Park are located nearby.
Foster's Inn

Foster's Inn

Stratford City Centre
$1,196
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Toronto (YYZ)
Stay at this inn in Stratford. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Festival Theatre and Avon Theatre are located nearby.
Wonderful food, cute and stylish-very clean room, great bar and a very personable staff! Bonus an elevator and parking!

Reviewed on Sep 4, 2026

Edisons Inn

Edisons Inn

Stratford City Centre
$1,208
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Toronto (YYZ)
Stay at this guesthouse in Stratford. Enjoy free WiFi, free parking, and Netflix. Popular attractions Festival Theatre and Shakespearean Gardens are located nearby.
There is dedicated parking about a block from the property. The Music Suite I chose was on the second level, so a long flight of stairs (FYI). Self check in was easy with a digital door code. I would stay again.

Reviewed on Aug 29, 2026

Perth County Inn

Perth County Inn

Stratford City Centre
$1,203
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Toronto (YYZ)
Stay at this hotel in Stratford. Enjoy free WiFi, free parking, and a snack bar/deli. Popular attractions Festival Theatre and Shakespearean Gardens are located nearby.
A somewhat quirky property but very clean and very convenient. Our Tuesday night stay was very quiet.

Reviewed on Sep 3, 2026

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Collingwood Vacation Packages

Trying to plan a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Collingwood vacation packages can help. We're here to book everything you'll need to make your Collingwood trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. We have a huge choice of flights and hotels, and Collingwood things to do to pull from.

Hotel Deals in Collingwood

You can choose from around 1588 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Collingwood hot spots, we have plenty of options available.

We have great deals on everything from luxury hotels that meet all the vacation must-haves to inexpensive accommodations perfect for those on looking to save. You can search all the possibilities and pick the hotel that is ideal for you. With AARP Travel Center's Collingwood hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Collingwood

The fact that you are traveling to Collingwood means your holiday will already be off to a great start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.

If you're making this a family getaway, then you are in luck. Collingwood has a theme park close by. You can spend an afternoon at Blue Mountain Go Karts riding rides, playing games, and amusing the kid in everyone.

If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.

Book Together and Save

With so much to see and do in Collingwood, you'll be wanting to focus on your itinerary, not devoting time to finding the hotel with the lowest rate. The AARP Travel Center Powered by Expedia® allows you to easily book everything you want, and save money doing it. You can coordinate your whole holiday, including activities in Collingwood from only one site. So what are you waiting for? Book now and save!

Top Hotel Deals

Living Stone Golf Resort

Living Stone Golf Resort

19 Keith Ave Collingwood ON
2.13 km from city center
Book a stay at this golf resort in Collingwood. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
Days Inn & Suites by Wyndham Collingwood

Days Inn & Suites by Wyndham Collingwood

15 Cambridge Street Collingwood ON
1.56 km from city center
Book a stay at this business-friendly hotel in Collingwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Living Water Resort and Spa

Living Water Resort and Spa

9 Harbour Street East Collingwood ON
1.73 km from city center
Book a stay at this spa resort in Collingwood. Enjoy an outdoor pool, a full-service spa, and a marina. Our guests praise the restaurant and the helpful staff ...
Georgian Bay Hotel Trademark Collection by Wyndham

Georgian Bay Hotel Trademark Collection by Wyndham

10 Vacation Inn Collingwood ON
4.1 km from city center
Stay at this resort in Collingwood. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. Popular ...
Holiday Inn Express & Suites Collingwood by IHG

Holiday Inn Express & Suites Collingwood by IHG

500 HUME STREET Collingwood ON
1.5 km from city center
Book a stay at this business-friendly hotel in Collingwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites

Comfort Inn & Suites

4 Balsam Street Collingwood ON
1.43 km from city center
Book a stay at this business-friendly hotel in Collingwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Dorchester Hotel

The Dorchester Hotel

174 Hurontario St Collingwood ON
0.27 km from city center
Stay at this hotel in Collingwood. Enjoy free WiFi, parking (surcharge), and cable TV channels. Our guests praise the helpful staff and the clean rooms in our ...
Candlewood Suites Collingwood by IHG

Candlewood Suites Collingwood by IHG

502 Hume Street Collingwood ON
1.6 km from city center
Stay at this hotel in Collingwood. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
Luxury Inn

Luxury Inn

530 First Street Collingwood ON
1.27 km from city center
Stay at this hotel in Collingwood. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
The Mariner Motor Hotel

The Mariner Motor Hotel

305 Hume St Collingwood ON
0.83 km from city center
Stay at this hotel in Collingwood. Enjoy free parking, room service, and a garden. Our guests praise the helpful staff and the overall value in our reviews. ...
Milestone Motel

Milestone Motel

327 First St Collingwood ON
0.81 km from city center
Stay at this motel in Collingwood. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
Downtown Collingwood Condos

Downtown Collingwood Condos

146 Hurontario St Collingwood ON
0.19 km from city center
Stay at this condo in Collingwood. Enjoy free WiFi and climate control. Popular attractions Blue Mountain Ski Resort and Scandinave Spa Blue Mountain are located ...
Relax Inn Collingwood

Relax Inn Collingwood

9448 Beachwood Road Collingwood ON
5.52 km from city center
Stay at this motel in Collingwood. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Somewhere Inn Collingwood

Somewhere Inn Collingwood

128 St Paul St Collingwood ON
0.26 km from city center
Stay at this hotel in Collingwood. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Blue Mountain Ski Resort and Scandinave Spa ...
Pleasant Manor Motel

Pleasant Manor Motel

9656 Beachwood Road Collingwood ON
4.55 km from city center
Stay at this motel in Collingwood. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Blue Mountain Go-Karts and Inukshuk Stone Sculpture ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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