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.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Excellent hotel with friendly staff, clean and comfortable rooms with a Starbucks! We love the cookies at check in. always a winner. It is in a weird location but for our one night it was great.

Reviewed on Jul. 14, 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! (1,018 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 9 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! (122 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 non-stop 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

Ready to book your vacation to Shirley?

 

Choose your dates

Shirley Hotel Deals

Bedford Plaza Hotel - Boston
Bedford Plaza Hotel - Boston
2.5 out of 5
340 Great Road, Bedford, MA
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 15 to Jul 16
CA $129
CA $145 total
Jul 15 - Jul 16
includes taxes & fees
7.2/10 Good! (318 reviews)
"If you are looking for a solid place to sleep with nothing fancy at all at a good deal, this is it. Felt safe felt clean that’s about it!"

Reviewed on Jul. 9, 2025

Bedford Plaza Hotel - Boston
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
DoubleTree by Hilton Hotel Boston - Westborough
DoubleTree by Hilton Hotel Boston - Westborough
4 out of 5
5400 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
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
8.6/10 Excellent! (1,010 reviews)
"Clean and renovated room with Hilton digital key entry, online check-in, and room selection supported. Double-Tree cookie was delicious!"

Reviewed on Jul. 12, 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 332 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

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Shirley vacation package cost?
Offering excellent value package deals from CA $631 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.