Winthrop Vacation Packages
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Your Winthrop Vacation
There's no better way to escape than with one of our vacation packages to Winthrop. The rich history and coastal scenery are a couple of the countless reasons to visit this captivating city. Fill your free time with tours of Boston Common, Faneuil Hall Marketplace and Copley Place, some of the top attractions you simply have to see during your trip to Winthrop. Check out Expedia's extensive range of travel options and start planning your ideal vacation to Winthrop now.
Top Winthrop Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $2,696, price is now CA $1,774 per person
CA $1,774
per person
May 16 - May 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
Life House, Nantucket
Nantucket Town
Price was CA $3,905, price is now CA $2,627 per person
CA $2,627
per person
Jun 24 - Jun 29
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (65 reviews)
The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again.
Reviewed on Sep 26, 2025
The Cove at Yarmouth by Westgate Resorts
Price was CA $1,685, price is now CA $1,164 per person
CA $1,164
per person
May 16 - May 22
found 22 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.2/10 Wonderful! (257 reviews)
From the moment we arrived, we was welcomed with warm hospitality and genuine friendliness
The room was spotless, comfortable, and beautifully maintained, and I especially appreciated the attention to detail throughout the property. The indoor pool a plus in these cold months -
The location was perfect as well—close to everything I wanted to explore, yet peaceful and relaxing.
Your staff went above and beyond to ensure a pleasant experience, and it did not go unnoticed. It’s clear that you take great pride in providing exceptional service, and it made my trip all the more memorable.
Thank you for such a wonderful stay. I will absolutely be recommending your hotel to friends and family, and I look forward to returning in the future.
Reviewed on Mar 29, 2026
Winthrop Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $269 per night from May 10 to May 11
CA $269
CA $370 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,583 reviews)
Room was amazing Just not a lot of restaurants or bars around hotel
Reviewed on Apr 11, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from May 10 to May 11
CA $209
CA $291 total
May 10 - May 11
includes taxes & fees
9.6/10 Exceptional! (4,179 reviews)
Great location. Amazing restaurants within walking distance. Easy to get to the Airport within 15 minutes
Reviewed on Apr 11, 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $290 per night from May 10 to May 11
CA $290
CA $394 total
May 10 - May 11
includes taxes & fees
8.4/10 Very Good! (3,151 reviews)
Great place, excellent location. Come back again for sure.
Reviewed on Apr 12, 2026
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.
Discover the most popular places to visit in Winthrop
Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Gillette Stadium
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theater scene.
What to do in Winthrop
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $115
per adult
92% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
CA $49
per adult
98% of travellers recommend
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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.
