Wayland Vacation Packages

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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

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,004, price is now CA $517 per person
CA $517
per person
Oct 28 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,679, price is now CA $1,464 per person
CA $1,464
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
Lovely property and staff. Great location and spa. Will return!

Reviewed on Aug. 26, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,625, price is now CA $956 per person
CA $956
per person
Oct 31 - Nov 2
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (482 reviews)
Love the Street Bar!

Reviewed on Aug. 25, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,976, price is now CA $1,278 per person
CA $1,278
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug. 24, 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Price was CA $1,891, price is now CA $1,269 per person
CA $1,269
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,326 reviews)
Nos encanta este hotel y siempre volvemos.

Reviewed on Aug. 24, 2025

Ready to book your vacation to Wayland?

 

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Wayland Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Sep 1 to Sep 2
CA $223
CA $267 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,276 reviews)
"Clean comfortable room with massive comfy bed. Very conveniently situated for the cruise port. Staff were extremely professional, friendly and helpful."

Reviewed on Aug. 25, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $295 per night from Sep 1 to Sep 2
CA $295
CA $400 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,870 reviews)
"We stayed for a couple of days at the end of our trip to Boston, the hotel was perfect for relaxing by the pool and a short walk from all the areas we wanted to see whilst visiting."

Reviewed on Aug. 25, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Sep 1 to Sep 2
CA $254
CA $295 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,709 reviews)
"So modern, clean and comfortable"

Reviewed on Aug. 27, 2025

citizenM Boston North Station
See all 3,472 properties in Wayland
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Wayland

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Wayland

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Wayland

Frequently asked questions

How much does a Wayland vacation package cost?
You can snap up a vacation package to this top destination from CA $517 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.