Medway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Beth Comstock

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Your Medway Vacation

Planning your next break is a piece of cake with a Medway vacation package. The neighborhood of Blackstone, which is good for history, makes a terrific base to uncover the delights of this city. If your trip to Medway includes a little sightseeing, take in popular attractions like Dean College, Medfield Meadow Lots and Franklin Public Library. Expedia is here to help you escape the everyday. Tailor your vacation to Medway to match your travel style, whatever that may be!

Top Medway 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 $1,008, price is now CA $536 per person
CA $536
per person
Nov 1 - Nov 3
found 19 hours 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 $3,757, price is now CA $2,165 per person
CA $2,165
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,269, price is now CA $2,097 per person
CA $2,097
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
The staff were amazing, rooms were spotless and with wonderful amenities and special touches.

Reviewed on Aug. 22, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was CA $2,161, price is now CA $1,430 per person
CA $1,430
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Heather was unbelievable in every way. Because of her past excellent service we returned!! She makes this hotel experience a true pleasure. Thank you Heather for your kind and gracious assistance.

Reviewed on Aug. 21, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,455, price is now CA $967 per person
CA $967
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Great Experience at a great location

Reviewed on Aug. 21, 2025

Ready to book your vacation to Medway?

 

Choose your dates

Medway Hotel Deals

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street, Newton, MA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Sep 1 to Sep 2
CA $170
CA $190 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (2,866 reviews)
"All good"

Reviewed on Aug. 20, 2025

Four Points by Sheraton Boston Newton
Embassy Suites by Hilton Boston Waltham

Embassy Suites by Hilton Boston Waltham

3.5 out of 5
550 Winter Street, Waltham, MA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Sep 5 to Sep 6
CA $175
CA $196 total
Sep 5 - Sep 6
includes taxes & fees
7.8/10 Good! (2,301 reviews)
"Dining table chairs need to change immediately."

Reviewed on Aug. 21, 2025

Embassy Suites by Hilton Boston Waltham
Sheraton Boston Needham Hotel

Sheraton Boston Needham Hotel

3.5 out of 5
100 Cabot St, Needham, MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Aug 31 to Sep 1
CA $199
CA $222 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,480 reviews)
"The hotel was very convenient to the highway for our many travels around the Boston area. Clean rooms, courteous staff."

Reviewed on Aug. 21, 2025

Sheraton Boston Needham Hotel
See all 982 properties in Medway
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

Frequently asked questions

How much does a Medway vacation package cost?
You can pick up a vacation package to this popular destination from CA $536 on Expedia. But how much your vacation to Medway costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Medway?
If you're hoping to book a cheap Medway vacation package, consider travelling in January, February and March. You'll typically find better prices on flights and accommodations during these months — perfect for a budget-friendly getaway.
How many days is enough for Medway?
With a well-organized schedule, you can easily visit the top Medway attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Medway vacation for longer.
How to find the best Medway package deals?
Begin your search for a Medway package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Medway package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Medway adventure underway.
Is it cheaper to book a Medway vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a personalized Medway vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Medway?
If you have your Medway vacation dates locked in, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Medway?

  1. Choose your travel dates: What you plan to do in Medway and your preferred season will help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and activities. Your accommodations will probably be the largest expense during your trip to Medway.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Medway. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Medway vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.