Midland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

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

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

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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 Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $1,092, price is now CA $783 per person
CA $783
per person
Mar 14 - Mar 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,201, price is now CA $1,490 per person
CA $1,490
per person
Apr 3 - Apr 6
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,572, price is now CA $1,194 per person
CA $1,194
per person
Apr 3 - Apr 6
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $1,186, price is now CA $902 per person
CA $902
per person
Mar 14 - Mar 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Staff was great! Still playing Christmas Music in the ballrooms where meetings are held. Food at the meeting was great! Great bar! Great location to Back Bay.

Reviewed on Jan 30, 2026

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Price was CA $1,233, price is now CA $944 per person
CA $944
per person
Mar 14 - Mar 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (2,315 reviews)
All around excellent experience.

Reviewed on Feb 6, 2026

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 $220 per night from Feb 16 to Feb 17
CA $220
CA $255 total
Feb 16 - Feb 17
includes taxes & fees
8.8/10 Excellent! (2,912 reviews)
Very accommodating and great location

Reviewed on Feb 4, 2026

Omni Providence Hotel
The Verve Hotel Boston Natick, Tapestry Collection by Hilton

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

3.5 out of 5
1360 Worcester St Natick MA
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Feb 22 to Feb 23
CA $147
CA $164 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
The atmosphere is really cool! Ellen who checked us in was exceptional, friendly and engaging. Ed the bartender at violet thorn was great, drinks were delicious especially the expresso martini! He was friendly and loved his stories!

Reviewed on Jan 31, 2026

The Verve Hotel Boston Natick, Tapestry Collection by Hilton
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 $85 per night from Feb 17 to Feb 18
CA $85
CA $144 total
Feb 17 - Feb 18
includes taxes & fees
8.4/10 Very Good! (1,205 reviews)
THE BED!! Its all about the bed and Bally's has the most comfortable and cozy bed I've ever slept in....better than home..thats the truth!! Room is always spotless and I always just fall into the bed, wish I could sleep here everynight, thank you

Reviewed on Feb 2, 2026

Bally's Twin River Lincoln Casino & Hotel
See all 654 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.
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Frequently asked questions

How much does a Midlands vacation package cost?
Live it up in Midlands from as little as CA $783. 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.