Pembroke Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Pembroke Vacation

Reserve a Pembroke vacation package and get set to experience all this city has to offer. Consider staying in the neighborhood of Plymouth Cultural District, which is great for dining, culture and history. Fill up your itinerary with visits to Rockland Ice Rink, Marshfield Country Club and Cranberry Watershed Preserve, some of the things you really should see during a trip to Pembroke. A few clicks is all it takes to craft a tailored Pembroke vacation on Expedia.

Top Pembroke Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,085, price is now CA $781 per person
CA $781
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)
The hotel was well maintained, staff was great. Saw a cockroach in the lobby at check in, but the hotel appeared to be clean. Great location near td garden and train station.

Reviewed on Nov 14, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,103, price is now CA $1,202 per person
CA $1,202
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $1,380, price is now CA $837 per person
CA $837
per person
Jan 29 - Jan 31
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,506, price is now CA $1,043 per person
CA $1,043
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
This was a return visit by my husband and myself to the Langham Hotel in Boston. The hotel is beautifully maintained and the staff was incredibly attentive. Our room was upgraded and was ready when we arrived. Breakfast at one of the two restaurants, Grana, was also special and waitstaff was equally attentive, even though the restaurant was very busy. All-in-all, our weekend at this hotel was lovely!

Reviewed on Nov 15, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $1,809, price is now CA $1,361 per person
CA $1,361
per person
Jan 29 - Jan 31
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Everything was great except the view from my room. Overlooking a carpark was not what one would expect staying with RAFFLES. Maybe paint a beautiful mural on the walls of the parking infrastructure?

Reviewed on Nov 15, 2026

Ready to book your vacation to Pembroke?

 

Choose your dates

Pembroke Hotel Deals

Ramada by Wyndham Boston

Ramada by Wyndham Boston

2.5 out of 5
800 Morrissey Blvd Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Dec 13 to Dec 14
CA $138
CA $161 total
Dec 13 - Dec 14
includes taxes & fees
Ramada by Wyndham Boston
Garner Hotel Brockton - Boston by IHG

Garner Hotel Brockton - Boston by IHG

2.5 out of 5
405 Westgate Dr. Brockton MA
Fully refundable
The price is CA $141 per night from Dec 13 to Dec 14
CA $141
CA $158 total
Dec 13 - Dec 14
includes taxes & fees
8.6/10 Excellent! (1,349 reviews)
"Hotel was clean, friendly staff Got us in our room early"

Reviewed on Nov 15, 2026

Garner Hotel Brockton - Boston by IHG
Hyatt Place Boston/Braintree

Hyatt Place Boston/Braintree

3.5 out of 5
50 Forbes Road Braintree MA
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Nov 19 to Nov 20
CA $144
CA $161 total
Nov 19 - Nov 20
includes taxes & fees
Hyatt Place Boston/Braintree
See all 1,066 properties in Pembroke
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
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Beach Vacations
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Family Vacations
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Stay near popular Pembroke attractions

Soundcheck Studios

You can enjoy a show at Soundcheck Studios on your trip to Pembroke.
See properties

Frequently asked questions

How much does a Pembroke vacation package cost?
You'll find cheap prices from CA $781 on Expedia for your Pembroke escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Pembroke costs.
What are the cheapest months to go to Pembroke?
The off-season is the best time to travel to Pembroke if you're trying to keep costs down. Another tip for getting cheap Pembroke vacation packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Pembroke?
With around 2 days, you'll have enough time to experience popular neighbourhoods like North Pembroke and West Hanover during your Pembroke vacation. Make sure to also add Two Mile Farm and Green Harbour Golf Club to your sightseeing itinerary. Searching for more adventures? Consider exploring outside of Pembroke on day trips and tours.
How to find the best Pembroke package deals?
Start your search for a Pembroke package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Pembroke package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Pembroke getaway off to a flying start.
Is it cheaper to book a Pembroke vacation as a package?
You can enjoy significant savings on your next Pembroke retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Pembroke?
If you've got your Pembroke travel dates locked in, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Pembroke?

  1. Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to vacation in Pembroke.
  2. Set a budget: Factor in expenses such as flights, food and transportation when working out how much to put aside for your trip to Pembroke. Then, choose a property that works with your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you know more about Pembroke, you can work out the ideal length of your break. Create a draft plan and give yourself enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Pembroke vacation package that brings all your bookings together.

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