Midland Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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Your Midlands Vacation

When you book a vacation package to Midlands, you can relax and enjoy your escape knowing your travel plans have been worked out ahead of time. Discover the charms of this city while staying in a neighborhood like Blackstone, which is great for history. When the time comes to head out and see the sights, be sure to include Southwicks Zoo and Cormier Woods on the to-do list for your trip to Midlands. Your ultimate Midlands vacation is just a few clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored just for you.

Top Holiday Package Deals in Midland

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was CA $917, price is now CA $633 per person
CA $633
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,156 reviews)
Absolutely loved it all- hip new vibe. Easy going staff at the ready. Gorgeous rooms and the ‘down the hall bathroom’ was across from room and all amenities perfect. Private bathroom suites. Parking right around the corner. Such a good 24 hours in Boston!

Reviewed on Sep 13, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,848, price is now CA $1,666 per person
CA $1,666
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (159 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep 2, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $1,306, price is now CA $862 per person
CA $862
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
It’s still the best hotel in Cambridge

Reviewed on Sep 12, 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 $1,365, price is now CA $918 per person
CA $918
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,334 reviews)
Great service! From the moment we checked in till the time we checked out we had an amazing experience.

Reviewed on Sep 13, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,058, price is now CA $716 per person
CA $716
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,015 reviews)
Great place for families to stay when moving your young adults to Boston for college or from one apartment to another. Located close to Harvard, MIT, Boston University, Tufts University, Cambridge, Allston, Storrow Drive easy access to drive to Boston MFA and Isabella Stewart Gardner Museum

Reviewed on Sep 13, 2025

Midland Hotel Deals

Omni Providence Hotel

Omni Providence Hotel

4 out of 5
1 W Exchange St, Providence, RI
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Sep 30 to Oct 1
CA $219
CA $252 total
Sep 30 - Oct 1
includes taxes & fees
Omni Providence Hotel
Bally's Twin River Lincoln Casino & Hotel

Bally's Twin River Lincoln Casino & Hotel

3.5 out of 5
100 Twin River Rd, Lincoln, RI
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Sep 22 to Sep 23
CA $136
CA $200 total
Sep 22 - Sep 23
includes taxes & fees
Bally's Twin River Lincoln Casino & Hotel
Courtyard by Marriott Boston Natick

Courtyard by Marriott Boston Natick

3 out of 5
342 Speen St, Natick, MA
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Sep 21 to Sep 22
CA $165
CA $184 total
Sep 21 - Sep 22
includes taxes & fees
Courtyard by Marriott Boston Natick
See all 564 properties in Midland
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 Midlands vacation package cost?
Live it up in Midlands from as little as CA $633. Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. Land even more discounts when you add a few tours or experiences to your package.
How do I get a cheap travel package to Midlands?
You'll save loads of cash if you combine your car rentals, hotels and flights into a Midlands travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer more than 550 air carriers and 1,000,000 hotels throughout the world, so you'll always have plenty of variety to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
How far in advance should I book my Midlands vacation?
While prices change frequently, we generally suggest booking your spot as soon as possible. Many international airfares become available on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you may still get lucky. Cheaper tickets to Midlands sometimes occur only weeks before departure.
What does an Expedia Midlands travel package include?
Hotels, flights and a shiny set of wheels for your road trip adventures. Simply choose your favorite bundle and gain access to great discounts. Once you've made your booking, add on a few sightseeing tours and watch your savings pile up. When it comes to organizing your Midlands getaway, the choice is all yours!
What should I know before booking a Midlands travel package?
You can save a tidy sum by bundling your hotels, flights and rental cars. Once you've created your package, you can add on things like tours and activities. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Midlands Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Midlands vacation package?
Because we understand life can be unpredictable, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you've booked your Midlands vacation package in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.