Shirley Vacation Packages

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Your Shirley Vacation

When you book a Shirley vacation package, it's all about letting go and enjoying your adventure to the fullest. Delve into the highlights of this lively city knowing that everything has been taken care of before you go. Any trip to Shirley needs a well-planned itinerary. Fill yours with leading attractions like The Mall at Whitney Field, Nashoba Paddler and Harvard Town Beach. Stop dreaming and start adventuring. Explore the wide range of options on Expedia today and put your Shirley vacation plans into gear!

Top Shirley 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
per person
Nov 1 - Nov 3
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 11 - Oct 13
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great location, wonderful customer service!

Reviewed on Aug. 18, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Oct 21 - Oct 24
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug. 11, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Oct 21 - Oct 24
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
The beds are the main thing that keep me coming black, so comfortable, especially after a long day of walking around Boston. I will say we were disappointed that the inside of our coffee machine was very dirty.. something i think shouldn't be missed when cleaning since we love a good morning coffee in the room , but had to settle for going to a coffee shop. We tried ordering room service , but after waiting over 1hr we ended up calling to cancel it. For the amount of money we paid , i think they could step their game up when it comes to service and details.

Reviewed on Aug. 16, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9.4/10 Exceptional! (360 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on Aug. 4, 2025

Ready to book your vacation to Shirley?

 

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Shirley Hotel Deals

Bedford Plaza Hotel - Boston

Bedford Plaza Hotel - Boston

3 out of 5
340 Great Road, Bedford, MA
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Aug 19 to Aug 20
CA $146
CA $163 total
Aug 19 - Aug 20
includes taxes & fees
7.4/10 Good! (404 reviews)
"This hotel has been on our to-stay list for years and it rarely disappoints, This time we were in need of emergency medical service and that went perfectly smoothly. Clean, comfortable, a little dated in its room style, but usually without any issues. When I have had issues, they have always been ..."

Reviewed on Aug. 13, 2025

Bedford Plaza Hotel - Boston
Courtyard by Marriott Boston Marlborough

Courtyard by Marriott Boston Marlborough

3 out of 5
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Aug 24 to Aug 25
CA $149
CA $166 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Great room, clean- modern Tv, shower ++"

Reviewed on Aug. 18, 2025

Courtyard by Marriott Boston Marlborough
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Aug 20 to Aug 21
CA $199
CA $222 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"This is a greag property with plenty of historic charm. The staff are all friendly and helpful. This was my second stay here and I'll definitely be back."

Reviewed on Aug. 17, 2025

The Colonial Hotel
See all 333 properties in Shirley
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
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Frequently asked questions

How much does a Shirley vacation package cost?
Offering excellent value package deals from CA $760 on Expedia, you'll be pleasantly surprised at how much a vacation to Shirley costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Shirley?
You can generally find reduced prices and better availability in January, February and November. Browse our cheap Shirley vacation packages and you could score some great off-season deals.
How many days is enough for Shirley?
With a well-organized schedule, you can easily tick off the main Shirley sights in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Shirley vacation for longer.
How to find the best Shirley package deals?
Use Expedia's filter tool to help you find some fabulous Shirley package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Shirley package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Shirley vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can personalize your Shirley getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Shirley?
If you're considering a spur-of-the-moment Shirley vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Shirley?

  1. Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the available activities will also help you decide when to escape to Shirley.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to activities and flights. Your accommodations will likely be the largest expense during your trip to Shirley.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Shirley. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the perfect Shirley vacation package for you.

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