Prospect Hill Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Prospect Hill

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,424, price is now CA $942 per person
CA $942
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on Feb 2, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,157, price is now CA $2,327 per person
CA $2,327
per person
Apr 27 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $4,358, price is now CA $2,939 per person
CA $2,939
per person
Apr 29 - May 3
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Attention to guest needs.

Reviewed on Feb 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,560, price is now CA $1,065 per person
CA $1,065
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $1,818, price is now CA $1,254 per person
CA $1,254
per person
Mar 21 - Mar 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.

Reviewed on Feb 7, 2026

Where to stay in Prospect Hill

Find the best Prospect Hill areas and neighborhoods for the activities you enjoy most. Learn more about Prospect Hill
Downtown Boston showing a city and night scenes 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 hotels in Downtown Boston

Prospect Hill Hotel Deals

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 $131 per night from Feb 22 to Feb 23
CA $131
CA $208 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (3,113 reviews)
The hotel itself is beautiful. The lobby is grand with a vibrant bar, restaurant in the center. The staff is friendly. This was a weekend away for me and my 10 year old daughter and we wanted something luxurious. Since it was so cold outside I knew we were going to be in the room a lot. I know the ...

Reviewed on Feb 6, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is CA $145 per night from Feb 16 to Feb 17
CA $145
CA $169 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (6,199 reviews)
Best price for the location! Always clean and great staff!

Reviewed on Feb 4, 2026

Harborside Inn Of Boston
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 $121 per night from Mar 10 to Mar 11
CA $121
CA $141 total
Mar 10 - Mar 11
includes taxes & fees
9/10 Wonderful! (2,451 reviews)
I stayed in a loft on the side of the main hotel, and it was extremely spacious with all the amenities I needed. It was definitely worth the price, especially given the beautiful area it’s located in. I didn’t interact much with the staff, but the few interactions I had were very pleasant. I would ...

Reviewed on Feb 7, 2026

The Revolution Hotel
See all 4,169 properties in Prospect 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.
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All Inclusive Vacations
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Frequently asked questions

How much does a Prospect Hill vacation package cost?
Go from wondering to wandering with our Prospect Hill vacation packages, which start from just CA $942. Choose the flights and hotels that suit your travel style. Then, add on some activities or tours for an unforgettable adventure.
How do I get a cheap travel package to Prospect Hill?
You'll save a ton of money if you bundle your car rentals, flights and hotels into a Prospect Hill travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels across the globe, so you'll always have plenty of options to choose from. Want to save even more? Add some popular activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Prospect Hill?
A getaway to Prospect Hill isn't complete without paying a visit to Assembly Row, LEGOLAND® Discovery Center and Somerville Theatre. Stay close to these popular attractions and make sightseeing a breeze.
How far in advance should I book my Prospect Hill vacation?
While not all air carriers advertise ticket prices early, customers are usually able to compare international airfares on Expedia up to a year in advance. This is the time you'll nab some incredible deals. If you're purchasing tickets last minute, you could still be in luck. Low prices occasionally emerge a few weeks prior to departure.
What does an Expedia Prospect Hill travel package include?
You can select from a combination of hotels, rental cars and flights. Once you've made your booking, you can also add on experiences and activities. Want to pick your fare class? That's also possible. The choice is all yours when it comes to creating your perfect Prospect Hill getaway.
What should I know before booking a Prospect Hill travel package?
A package can be easier on the bank balance than individually booking everything you need for your escape. For example, combine your flights, hotels and rental cars and land a great deal. Whatever your vacation goals are, you're sure to find a package that suits your budget.
Can I choose my airline with a Prospect Hill Expedia vacation package?
You can. We offer more than 550 airline partners across the globe, so select the carrier that suits your budget and travel needs.
If I'm not able to travel, can I cancel my Prospect Hill vacation package?
We totally understand that unexpected stuff happens. If you've booked a Prospect Hill vacation package and need to cancel or change it, we can help. We suggest visiting our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to amend or cancel your itinerary for free. If it's been longer than 24 hours, your hotel, airline or car rental company may impose a charge.

Discover the most popular places to visit in Prospect Hill

Roger Williams Statue - Rhode Island

Prospect Hill Park

Prospect Hill Park is just one of the places to see in Somerville, so why not enjoy the other things to explore during your travels? Experience the acclaimed art scene or attend a sporting event in this vibrant area.

Prospect Hill Park

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $72
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

CA $31
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.