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Sears Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Sears vacation deals

Price found within the past 48 hours. Click for updated prices.
  • 2 restaurants; lunch and dinner served
    Aug 29 - Aug 31

    The Iron Horse Hotel + Flight

    Fifth Ward
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,231 reviews)
    Roundtrip • Toronto (YTO) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,264
    CA $1,048
    per traveller
    found 1 day ago
    The Iron Horse Hotel
  • Garden
    Sept 30 - Oct 4

    Saint John's Resort + Flight

    Plymouth
    3 nights
    4.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    "Room was greatly clean. Check in staff was very helpful. This hotel is so beautiful. I always enjoy my stay over here."
    Reviewed July 21, 2026
    Roundtrip • Prince George (YXS) - Detroit (DTW)
    YXS - DTW • 2 stops DTW - YXS • 2 stops
    CA $3,187
    CA $2,185
    per traveller
    found 1 day ago
    Saint John's Resort
  • Lobby
    Aug 29 - Aug 31

    The Pfister Hotel + Flight

    Downtown Milwaukee
    2 nights
    4.5 star property
    9.6/10 - Exceptional (2,171 reviews)
    Roundtrip • Toronto (YTO) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,464
    CA $1,061
    per traveller
    found 2 days ago
    The Pfister Hotel
  • Exterior
    Sept 30 - Oct 4

    Trumbull and Porter Hotel + Flight

    Corktown
    3 nights
    3.5 star property
    8.4/10 - Very good (1,189 reviews)
    "No coffee, no free breakfast, no good furniture. Weird hotel."
    Reviewed July 24, 2026
    Roundtrip • Prince George (YXS) - Detroit (DTW)
    YXS - DTW • 2 stops DTW - YXS • 2 stops
    CA $1,561
    CA $1,288
    per traveller
    found 1 day ago
    Trumbull and Porter Hotel
  • Deluxe King
    Aug 29 - Aug 31

    Saint Kate - The Arts Hotel + Flight

    Downtown Milwaukee
    2 nights
    4.0 star property
    9.8/10 - Exceptional (2,637 reviews)
    Roundtrip • Toronto (YTO) - Milwaukee (MKE)
    YYZ - MKE • 1 stop MKE - YYZ • 1 stop
    CA $1,312
    CA $1,159
    per traveller
    found 2 days ago
    Saint Kate - The Arts Hotel

Discover the most popular places to visit in Sears

Tubs Lake

Commune with nature and explore the great outdoors at Tubs Lake during your travels in Sears.

Sears Hotel Deals

Exterior detail

Osceola Grand Hotel

Osceola Grand Hotel
2.5 star property
6.6 km from Sears
7.8 out of 10, Good, (384 reviews)
The price is CA $125
CA $133 total
includes taxes & fees
Jul 27 - Jul 28
Osceola Grand Hotel
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.
See all properties in Sears

Frequently Asked Questions

How much does a Sears vacation package cost?

You'll find cheap prices from CA $1,048 on Expedia for your Sears getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Sears costs.

What are the cheapest months to go to Sears?

The off-season is the best time to head to Sears if you're trying to keep costs down. Another tip for getting cheap Sears vacation packages? Avoid visiting during public holidays and any major events.

How many days is enough for Sears?

Typically, a handful of days is enough to go to the top sights during your Sears vacation. But if you'd like to have time to kick back or take day tours, think about extending your trip.

How to find the best Sears package deals?

Start your search for a Sears package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Sears package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sears escape underway.

Is it cheaper to book a Sears vacation as a package?

An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can customize your Sears getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to Sears?

If you have your Sears vacation dates finalized, book early to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for jetting off on a whim.

How to plan a trip to Sears?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to vacation in Sears.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will probably be the largest expense during your trip to Sears.
  3. Decide how long to go away for: Now that you're more familiar with Sears, you can figure out the perfect length of your break. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the right Sears vacation package for you.

Book with confidence

Things to do in and around Sears

Sears, Michigan, offers a delightful escape for outdoor and romantic getaways, featuring a range of activities such as golf, serene resorts, and a recreational area. Enjoy night adventures, indulge in culinary tourism, or explore the area's kayaking paradise. Relax in swing chairs or take a scenic river ride to fully immerse yourself in the stunning surroundings. This charming destination is perfect for those seeking both adventure and tranquility.

Shopping

For a charming shopping experience, visit local shops like P&J Plantiques, located 38.6km away from Sears. If you're up for a drive, this store offers unique gifts and souvenirs that reflect the local culture and craftsmanship.

Recreation

In Sears, Birch Valley Golf Course invites you to enjoy a day of sport amidst beautiful outdoor scenery. A short drive away, Clear Lake Golf Club offers a similar experience. For relaxation, visit Grove Hill Park, where you can unwind in a serene recreational area.

Adventure

Explore the scenic White Pine Trail State Park, perfect for hiking 30.6km from Sears. Hit the slopes at Snow Snake Ski and Golf, located 33.8km away, for thrilling skiing experiences. For family fun, visit Adventure Island Family Fun Park, an exciting arcade adventure zone 43.5km from Sears.

Nightlife

Sears offers a charming nightlife with cozy spots like The Corner Bar, perfect for a laid-back drink with locals. For a lively atmosphere, check out the Lakefront Lounge, where you can enjoy live music and dance the night away under the stars.

Find the best attractions in and around Sears

Sears, Michigan, is perfect for outdoor and romantic getaways, offering stunning scenery and opportunities to explore lakes, modern civic buildings, and nature reserves. Visitors can enjoy a variety of attractions that cater to those seeking beach experiences and beautiful landscapes. Don't miss the chance to discover the best local beaches for a memorable experience during your stay in this charming area.

  • Eight Point Lake: Located 11.3km from Sears, this picturesque lake offers stunning scenery and a beach perfect for relaxation. Ideal for a romantic getaway or outdoor activities, you can enjoy swimming, picnicking, or simply soaking in the tranquil atmosphere.
  • Orient Township Hall: Situated within Sears, this modern civic government building reflects the town's commitment to community and governance. It’s a hub for local business and civic engagement, offering a glimpse into the administrative heart of the area.
  • Neithercut Woodland: A nature reserve located 20.9km from Sears, Neithercut Woodland invites you to explore its eco-friendly trails and embrace adventure. Perfect for hiking and wildlife observation, it’s an outdoor paradise for nature enthusiasts.

Best time to go to Sears

The best time to visit Sears is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is very cloudy with no rain.

Tips to save on your trip to Sears

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Sears.
  • Consider traveling during the off-peak season (typically November to January) for more affordable package holidays to Sears.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.