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.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Aug. 27 - Aug. 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.4/10 Very Good! (3,336 reviews)
Close to Public Gardens.

Reviewed on Jun. 15, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Aug. 11 - Aug. 16
found 5 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Absolutely wonderful!

Reviewed on Jun. 11, 2024

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug. 13 - Aug. 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (2,257 reviews)
Loved the modern, clean, smoke free environment. Excellent gym, slightly disappointed that there is no pool.

Reviewed on Jun. 16, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 26 - Aug. 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (34 reviews)
Beautiful hotel, flowers in All areas. Staff was superb. Two very minor issue - no fan for toilet area, hot water in shower takes a bit. Doesn’t distract from my overall rating. Easily a come back recommendation

Reviewed on May 29, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 18 - Aug. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
EVERYTHING is thought out. Service is “old world”. Attention to details is magnificent. What’s there not to like.

Reviewed on Jun. 9, 2024

Winthrop Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $308 per night from Jul. 6 to Jul. 7
CA $308
CA $406 total
includes taxes & fees
Jul 6 - Jul 7
9/10 Wonderful! (2,066 reviews)
"Loved this hotel! Staff were awesome! So many staff. Also used spa and ate at the Sporting Club (which was also great except for the runner who slammed our food down in the wrong places without a care). Looking forward to trying more Omni hotels in the future."

Reviewed on Jun. 16, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $250 per night from Jul. 4 to Jul. 5
CA $250
CA $339 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,695 reviews)
"This hotel was right in the heart of Boston. The Freedom Trail is right out the door. We enjoyed our stay so much and look forward to staying there again when we visit Boston! So many restaurants, bars and shopping right by Hotel!"

Reviewed on Jun. 13, 2024

Omni Parker House
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Jun. 30 to Jul. 1
CA $219
CA $255 total
includes taxes & fees
Jun 30 - Jul 1
8.6/10 Excellent! (1,553 reviews)
"Such a fun and unique hotel! Great staff, super clean, really good location. The bathrooms were great as well, very clean. Only thing that disappointed was the wifi was really slow in our corner room."

Reviewed on Jun. 14, 2024

The Revolution Hotel
See all 3,269 properties in Winthrop
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 Winthrop vacation package cost?
Starting from an incredible CA $541, you can tailor make your Winthrop vacation package. Simply combine hotels, flights and rental cars and be rewarded with discounts.
How do I get a cheap travel package to Winthrop?
Browse and book everything in one place with our Winthrop vacation packages. We have deals on flights, hotels and more that’ll keep your credit card happy and your adventurous spirit alive. And, with more than 550 airlines and 1,000,000 hotels worldwide to select from, you’ll have the flexibility to mix and match however you please.
Where should I stay in Winthrop?
You’ll want to stay where the action is. Many travelers favor hotels within easy reach of top attractions, like Revere Beach, Revere Beach Reservation and Winthrop Beach.
What are the top hotels in Winthrop?
Château Sur Mer Bed And Breakfast and Casa De Los Clarey Boston Airport Beaches Off Street Parking Available are among the most well-known hotels in Winthrop. Why not look up the amenities and rates at each and then make a decision?
How far in advance should I book my Winthrop vacation?
It’s hard to pick the perfect time for airfares, but we generally suggest the earlier, the better. Most international journeys on Expedia become available to compare up to a year in advance. If you’re booking last minute, don’t worry. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Winthrop travel package include?
Expedia has all you need to book your Winthrop escape, but how you structure your package is your call. Select from any combination of flights, rental cars and hotels. Looking for some activities or tours to fill in your time? Once you’ve made your booking, you can add them on too. Whatever your budget, there’s a package deal to suit your needs.
What should I know before booking a Winthrop travel package?
Discover deals that match your budget with an Expedia package. Airfares, hotels, rental cars — we’ve got all of them. You’ll save big dollars just for combining your bookings. Whether you’re heading away on a ski adventure or venturing someplace warm, your ideal getaway is only a few clicks away.
Can I choose my airline with a Winthrop Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Winthrop vacation package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can change or cancel your Winthrop vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Winthrop

Image for Fenway Park

Fenway Park

4.5/5(305 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Image for Harvard University

Harvard University

4.5/5(279 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Image for Gillette Stadium

Gillette Stadium

4.5/5(27 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium

What to do in Winthrop

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $100
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

CA $41
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $186
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Winthrop
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.