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.
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Everything outstanding

Reviewed on Jul. 19, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 19 - Sep 22
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on Jul. 23, 2025

Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,033 reviews)
Was not aware of additional fees when arrived Room wasn’t ready after 4pm

Reviewed on Jul. 21, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 1 - Sep 5
found 11 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
The space was impeccably clean, and the warmth and friendliness of the people made for a truly delightful experience. Everything was fantastic; however, I did find the bathtub to be quite small, which was a bit of a drawback.

Reviewed on Jul. 24, 2025

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Wayland Hotel Deals

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 $244 per night from Aug 24 to Aug 25
CA $244
CA $339 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,715 reviews)
"The staff is absolutely exceptional! From the valet, to the front desk, to the restaurant staff, they go above and beyond to make our experience special! So thoughtful and so accommodating!"

Reviewed on Jul. 24, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $257 per night from Aug 10 to Aug 11
CA $257
CA $299 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,487 reviews)
"Great place. Just be prepared that there is no curb drop off or hotel parking, so figure out how you are going to park and get your suitcases there ahead of time. Very modern, good restaurant/coffee bar and large hangout lobby, 10 min walk to Finway area. Highly recommend."

Reviewed on Jul. 23, 2025

citizenM Boston Back Bay
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 $237 per night from Aug 24 to Aug 25
CA $237
CA $276 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (3,578 reviews)
"It was wicked awesome"

Reviewed on Jul. 24, 2025

citizenM Boston North Station
See all 3,451 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

4.5/5(305 reviews)

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

4.5/5(279 reviews)

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

4.5/5(518 reviews)

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 $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
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 $46
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 $1,060 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.