Winter Hill Vacation Packages

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Top Holiday Package Deals in Winter Hill

Price found within the past 48 hours. Click for updated prices.
Holly Tree Resort by VRI Americas

Holly Tree Resort by VRI Americas

3 out of 5
per person
Jul. 7 - Jul. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (300 reviews)
Loved this property

Reviewed on May 22, 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 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (270 reviews)
Awesome, awesome, awesome. I could not find another word to describe my stay! Awesome.

Reviewed on May 22, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 18 - Aug. 21
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (31 reviews)
My stay was lovely. In ordering a cheese plate to await my arrival, a friend alerted the staff that it was my birthday. When I entered my very handsome room, a gorgeous little chocolate bday cake, under domed glass, sat waiting for me. Otherwise, the staff was incredibly attentive, the speakeasy was fun for a delicious cocktail, and the overall atmosphere was one of restrained indulgence. The place doesn’t feel ostentatious. Its elegance was much more understated. I loved it

Reviewed on Apr. 28, 2024

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Aug. 7 - Aug. 11
found 18 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Impressive lobby, disappointing rooms … urgent refurbish needed !

Reviewed on May 18, 2024

The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug. 7 - Aug. 11
found 18 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.2/10 Wonderful! (3,500 reviews)
We had a wonderful time staying at Dagny! We haven’t had a chance to check out the gym, but the room and the staff was awesome! Will definitely stay there again.

Reviewed on May 22, 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

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 $368 per night from Jun. 16 to Jun. 17
CA $368
CA $436 total
includes taxes & fees
Jun 16 - Jun 17
9.6/10 Exceptional! (2,162 reviews)
"All of the employees of the hotel were so wonderful and helpful, which made our stay at the hotel so great."

Reviewed on May 19, 2024

Seaport Hotel Boston
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 $239 per night from May 27 to May 28
CA $239
CA $318 total
includes taxes & fees
May 27 - May 28
9/10 Wonderful! (2,068 reviews)
"great property convenient location. I would say again"

Reviewed on May 21, 2024

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza
Hilton Boston Park Plaza
4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $259 per night from May 27 to May 28
CA $259
CA $357 total
includes taxes & fees
May 27 - May 28
8.4/10 Very Good! (3,325 reviews)
"Staff was very helpful. All recommendations were great."

Reviewed on May 23, 2024

Hilton Boston Park Plaza
See all 3,190 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

Beach Vacations

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 $602. 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 New England Aquarium

New England Aquarium

4.5/5(154 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $107
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
100% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

CA $264
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

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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.