Midland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

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

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.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

Midland Hotel Deals

Omni Providence Hotel
Omni Providence Hotel
4 out of 5
1 W Exchange St, Providence, RI
The price is CA $217 per night from Jul 27 to Jul 28
CA $217
CA $249 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (2,591 reviews)
"Nice hotel lots to do around the City."

Reviewed on Jul. 10, 2025

Omni Providence Hotel
Motel 6 Framingham, MA - Boston West
Motel 6 Framingham, MA - Boston West
2 out of 5
1668 Worcester Rd, Framingham, MA
Fully refundable
The price is CA $117 per night from Jul 16 to Jul 17
CA $117
CA $127 total
Jul 16 - Jul 17
includes taxes & fees
6.8/10 (1,011 reviews)
"Solid stay. Easy late night checkin"

Reviewed on Jul. 11, 2025

Motel 6 Framingham, MA - Boston West
Holiday Inn Boston - Dedham Hotel & Conference Center by IHG
Holiday Inn Boston - Dedham Hotel & Conference Center by IHG
3 out of 5
55 Ariadne Rd, Dedham, MA
Fully refundable
The price is CA $163 per night from Aug 3 to Aug 4
CA $163
CA $182 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"Free breakfast would be nice"

Reviewed on Jul. 12, 2025

Holiday Inn Boston - Dedham Hotel & Conference Center by IHG
See all 587 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 $705. 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.