Winter Hill Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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Top Holiday Package Deals in Winter Hill

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug. 4 - Aug. 9
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (217 reviews)
Beautiful room, amenities, service, snacks and coffee station.

Reviewed on May 26, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug. 2 - Aug. 6
found 20 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
This was a wonderful overnight stop in Boston. We will be back.

Reviewed on Jun. 17, 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 flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (37 reviews)
Great Hotel. Exceptional customer service very professional staff. Highly recommended.

Reviewed on Jun. 25, 2024

The Kendall Hotel

The Kendall Hotel

3 out of 5
MIT
Save 100% on your flight
per person
Aug. 4 - Aug. 9
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
Excellent service and hospitality. Clean and awesome decor throughout the property. Breakfast was delicious. Would highly recommend to anyone going to the Boston/Cambridge area.

Reviewed on Jun. 24, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 22 - Aug. 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (279 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

Where to stay in Winter Hill

Find the best Winter Hill areas and neighborhoods for the activities you enjoy most. Learn more about Winter Hill
Downtown Boston which includes night scenes and a city as well as a small group of people

Downtown Boston

4.5/5(193 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotel + flight trips in Downtown Boston

Winter Hill 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 $288 per night from Jul. 7 to Jul. 8
CA $288
CA $383 total
includes taxes & fees
Jul 7 - Jul 8
9/10 Wonderful! (2,262 reviews)
"Love the property and the service and the rooms were great too."

Reviewed on Jun. 25, 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 $247 per night from Jul. 7 to Jul. 8
CA $247
CA $336 total
includes taxes & fees
Jul 7 - Jul 8
8.8/10 Excellent! (2,691 reviews)
"Amazing stay! Staff were super friendly. Location is superb - walkable to so many attractions and sites"

Reviewed on Jun. 26, 2024

Omni Parker House
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $367 per night from Jul. 3 to Jul. 4
CA $367
CA $435 total
includes taxes & fees
Jul 3 - Jul 4
9.6/10 Exceptional! (2,275 reviews)
"Great and safe location. Lots of dining and shopping options in close walking distance. Clean rooms and very friendly staff. We had an early flight and was able to check in when we arrived."

Reviewed on Jun. 25, 2024

Seaport Hotel Boston
See all 3,179 properties in Winter Hill
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winter Hill vacation package cost?
We make it simple to see the world, with Winter Hill packages starting from just CA $1,459. You’ll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a few tours and activities to your travel itinerary?
How do I get a cheap travel package to Winter Hill?
Book everything in the one place with our Winter Hill vacation packages. We have deals on flights, hotels and more that’ll keep your pocket happy and your adventurous spirit alive. And, with more than 550 air carriers and 1,000,000 hotel options throughout the world to pick from, there are endless opportunities to mix and match.
Where should I stay in Winter Hill?
A trip to Winter Hill isn’t complete without stopping by Assembly Row, LEGOLAND® Discovery Center and Somerville Theatre. Spend your nights near these popular attractions and make sightseeing simple.
What are the top hotels in Winter Hill?
When it comes to comfy places to stay in Winter Hill, you can’t go past Top Floor Of One Family Home. Have a look at our deals and land a bargain.
How far in advance should I book my Winter Hill vacation?
Travelers are usually able to look up international airfares on Expedia within 12 months of the departure date. Booking last minute? With a little bit of luck, it’s still possible to nab a cheap ticket only weeks before your flight.
What does an Expedia Winter Hill travel package include?
From airfares and hotels to rental cars, Expedia can help you craft a Winter Hill package that’s ideal for you. Vacationing for a week or longer? Consider a rental car, flight and hotel bundle. If you’re taking a short break, a hotel and airfare deal may be more your style. Experiences can also be added once you’ve made your booking. Our vacation packages make it a breeze to save and plan.
What should I know before booking a Winter Hill travel package?
You’ll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up great discounts. Hotels aren’t your only option, however. Book with us and select from beachside condos, rural cottages and even ranches and treehouses!
Can I choose my airline with a Winter Hill Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Winter Hill vacation package?
It’s good to know that you can cancel your Winter Hill booking if your plans have changed. Whether you’ll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Discover the most popular places to visit in Winter Hill

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 great live music and acclaimed theater scene.

Gillette Stadium

Things to do

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 Boston

Other vacations you might like

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