Pembroke Vacations from $744
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The Latest Pembroke Vacation Packages
- By the Sea Guests Bed & Breakfast & Suites
Aug 27 - Aug 31By the Sea Guests Bed & Breakfast & Suites + Flight
Dennis Port4 nights3.5 star property9.4/10 - Exceptional (198 reviews)"The property was well maintained and close to good restaurants. We had a cooked breakfast every day."Reviewed July 16, 2026Roundtrip • Chicago (CHI) - Boston (BOS)ORD - ACK • 1 stop ACK - ORD • 1 stop - Nantucket Inn
Aug 27 - Aug 31Nantucket Inn + Flight
Nantucket4 nights3.5 star property9.2/10 - Wonderful (741 reviews)"Adorable, quaint place. Appreciated the shuttle. Staff at July 5 BBQ was awesome! However the check in staff was rude and definitely not helpful."Reviewed July 12, 2026Roundtrip • Chicago (CHI) - Boston (BOS)ORD - ACK • 1 stop ACK - ORD • 1 stop - Good Hotels Boston
Sep 24 - Sep 29Good Hotels Boston + Flight
South End5 nights2.0 star property8.0/10 - 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 May 23, 2026Roundtrip • Chicago (CHI) - Boston (BOS)ORD - BOS • Nonstop BOS - RFD • 1 stop - Boston Harbor Hotel
Aug 17 - Aug 20Boston Harbor Hotel + Flight
North End2 nights5.0 star property9.8/10 - Exceptional (1,001 reviews)"Great location and very helpful staff"Reviewed July 16, 2026Roundtrip • Burbank (BUR) - Boston (BOS)BUR - BOS • 1 stop BOS - BUR • 1 stop - Summer House Hotel
Aug 27 - Aug 31Summer House Hotel + Flight
Nantucket4 nights2.0 star property8.0/10 - Very Good (4 reviews)"Helpful staff! Make sure to review the check in information, there is a specific window of time! My room and bed were absolutely cozy and cute. I’d advise against staying in a cottage close to the restaurant in the summer if you are looking for absolute quiet due to the fact some are in immediate proximity to the outdoor dining area. Overall amazing stay, especially being so close to a beach with attached dining!"Reviewed July 15, 2026Roundtrip • Chicago (CHI) - Boston (BOS)ORD - ACK • 1 stop ACK - ORD • 1 stop
Where to stay in Pembroke
North Pembroke
North Pembroke offers a quintessential New England suburban experience away from urban hustle. This charming area features historic colonial homesteads and tree-lined streets that showcase authentic American neighborhood life. Conservation areas with walking trails wind through pristine ponds and wooded spaces, creating perfect spots for nature lovers. The peaceful community provides an intimate glimpse into suburban American living. Visitors can explore parts of the North River watershed or discover local historic sites dating back to colonial times. Nearby attractions like Two Mile Farm and Iron Mine Brook Nature Preserve make North Pembroke an ideal base for experiencing New England's natural beauty.
Discover the most popular places to visit in Pembroke
Pembroke Hotel Deals
Homestay In Fields Corner Area Boston
Homestay In Fields Corner Area Boston
Holiday Inn Express Plymouth by IHG
Holiday Inn Express Plymouth by IHG
Rodeway Inn Middleboro - Plymouth
Rodeway Inn Middleboro - Plymouth
Frequently Asked Questions
How much does a Pembroke vacation package cost?
You can snap up a vacation package to this popular destination from $744 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.