Pembroke Vacations from $653

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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.

The Latest Pembroke vacation packages

Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,046, price is now $653 per person
$653
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,507, price is now $850 per person
$850
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
From the moment I checked in with Natalie, our 4 days were superb! Natalie was so friendly and explained the property and amenities (our first time there). Even though I researched the property, and am originally from close to Boston, it was the 4th of July weekend, and there was Sooo much going on. Head concierge Nathan provided lots of tips about the best places to see certain events. So helpful. Our room was beautiful and well appointed. I miss the days of the shower cap, sewing kit, slippers, robes, etc. and they provided all that. The bed was extremely comfortable and the housekeeping staff wonderful. We go to Boston a few times a year and will be looking forward to returning here. Fabulous location!

Reviewed on Jul 8, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $5,471, price is now $3,391 per person
$3,391
per person
Aug 12 - Aug 17
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
Price was $1,275, price is now $791 per person
$791
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.2/10 Very Good! (2,436 reviews)
Nunca limpiaron el cuarto no cambiaron las toallas fuera de eso todo muy bueno

Reviewed on Jul 5, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,450, price is now $899 per person
$899
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

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Stay near popular Pembroke attractions

No Bottom Pond Area

This tranquil 2-acre fishing spot offers anglers a chance to catch largemouth bass and chain pickerel in a woodland setting. Visit during early morning hours when fish are most active and the mist rises off the water.
See properties

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
$106 nightly
The price is $123 total per night from Aug 2 to Aug 3
$123 total
Aug 2 - Aug 3
Total with taxes and fees
6.8/10 (1,779 reviews)
"Someone was in my room already. Very odd staff"

Reviewed on Jul 8, 2026

Ramada by Wyndham Boston
Marriott Boston Quincy

Marriott Boston Quincy

3.5 out of 5
1000 Marriot Dr Quincy MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Jul 12 to Jul 13
$142 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (1,455 reviews)
"The hotel was very clean and modern . Breakfast was good . Only thing I didn’t like was Paying for Parking . If I am a hotel quest where else would I park . Also coffee machine in n room did not work"

Reviewed on Jul 7, 2026

Marriott Boston Quincy
Best Western Adams Inn Quincy-Boston

Best Western Adams Inn Quincy-Boston

2.5 out of 5
29 Hancock St Quincy MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Jul 20 to Jul 21
$142 total
Jul 20 - Jul 21
Total with taxes and fees
7.6/10 Good! (1,180 reviews)
"Room was nice. Pub was great. Great dinner and atmosphere in the pub. Good breakfast"

Reviewed on Jul 7, 2026

Best Western Adams Inn Quincy-Boston
See all 1,079 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.

Find the Best Pembroke Vacation Packages

Pembroke Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Max Temp Winter
35ºF
Max Temp Summer
75ºF
Top Sights
Plymouth Long Beach, Mayflower II and Pilgrim Memorial State Park

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Frequently asked questions

How much does a Pembroke vacation package cost?
You can snap up a vacation package to this popular destination from $653 on Expedia. However, how much your vacation to Pembroke costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Pembroke?
If you're hoping to book a cheap Pembroke vacation package, consider visiting in November, December and January. You'll usually find better rates on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Pembroke?
The ideal length of your Pembroke vacation depends on what you'd like to see. Usually, a few days to a week will give you time to go to all the top sights and discover some hidden treasures along the way.
How to find the best Pembroke package deals?
Use Expedia's handy filters to find some great Pembroke package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Pembroke package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Pembroke vacation as a package?
You can enjoy significant savings on your Pembroke break by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Pembroke?
Score amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Pembroke trip.
Does Expedia offer Book Now, Pay Later Pembroke vacation packages?
Secure your ideal getaway to Pembroke with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up travel deals before they disappear.

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