Wayland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Your Wayland Vacation
Organizing your next big break is easy with a Wayland vacation package. The neighborhood of Auburndale, which is great for golfing, makes a good launchpad to uncover the treasures of this lively city. Make your trip to Wayland even more enjoyable by going sightseeing. Walden Pond, Wellesley College and Brandeis University are some of the most popular attractions you'll want to explore. Your perfect Wayland vacation is clicks away. Browse hotels, airfares and more on Expedia for a trip that's tailored to suit your style.
Top Wayland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $701
per person
Nov 8 - Nov 11
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
The apt was tidy. Enough to sleep 8. Bathrooms were clean and updated. Parking can be difficult to find. It's about an hour from Salem.
Reviewed on Oct 4, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,573
per person
Nov 26 - Nov 29
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
The Langham, Boston
Downtown Boston
CA $1,469
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The Langham is refined and just brilliant in guest services. Always looking to book with them where ever we travel, its just an assured luxurious and comfortable stay.
Reviewed on Oct 7, 2026
Ready to book your vacation to Wayland?
Wayland Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
CA $375
CA $495 total
Nov 1 - Nov 2
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $184
CA $214 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (2,949 reviews)
"Wonderful stay"
Reviewed on Oct 8, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $269
CA $361 total
Nov 8 - Nov 9
includes taxes & fees
9.6/10 Exceptional! (5,086 reviews)
"The front staff was the most impressive part of our stay. All were so helpful and so extremely kind in their assistance."
Reviewed on Oct 8, 2026
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 Wayland attractions
Wayland Town Beach
If a restful vacation is part of your travel plans, Wayland Town Beach might be the perfect place to seek out during your trip to Wayland. Amble around the area's lakeside or visit its shops.
What to do in Wayland
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $69
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $117
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
CA $65
per adult
80% of travellers recommend
Frequently asked questions
How much does a Wayland vacation package cost?
You can snap up a vacation package to this top destination from CA $701 on Expedia. But how much your vacation to Wayland costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Wayland?
January, February and November are the best times to search for cheap Wayland vacation packages. Travelling in quieter periods means you can generally find better prices on flights and hotels.
How many days is enough for Wayland?
With about 2 days, you'll have plenty of time to enjoy popular neighbourhoods like Auburndale and Highlands during your Wayland vacation. Be sure to also add Cochituate State Park and Shoppers World to your list of must-sees. Up for some more adventures? Consider exploring outside of Wayland on tours and day trips.
How to find the best Wayland package deals?
Bagging a cheap Wayland package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Wayland package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Wayland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can tailor your Wayland getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Wayland?
If you have your Wayland vacation dates confirmed, book early to bag some unbeatable deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Wayland?
- Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Wayland.
- Budget wisely: Besides the price of your hotel, you'll need to consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could arise during your trip to Wayland.
- Work out your trip length: Think about how long you want to spend discovering Wayland. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Wayland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
