Prospect Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Prospect Hill

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The air conditioner sound like a truck trailer was in your room

Reviewed on Jul. 11, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

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
Sep 1 - Sep 4
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

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 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 hotels in Downtown Boston

Prospect Hill Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $289 per night from Aug 10 to Aug 11
CA $289
CA $393 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,667 reviews)
"The hotel was clean and staff was friendly."

Reviewed on Jul. 12, 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Jul 20 to Jul 21
CA $252
CA $293 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,408 reviews)
"Always a great stay"

Reviewed on Jul. 11, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is CA $282 per night from Jul 20 to Jul 21
CA $282
CA $329 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (5,322 reviews)
"This is THE place to stay in Boston, the area is close to everything, the staff at the front desk and the restaurant Joia were beyond efficient and friendly, and although they didn't offer room service, they were more than accommodating to provide water, etc. for the room on the way up to to the ..."

Reviewed on Jul. 13, 2025

Harborside Inn Of Boston
See all 3,688 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $631. 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

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

Union Square, Somerville Neighborhood Food Tour

Union Square, Somerville Neighborhood Food Tour

CA $137
per adult
Union Square, Somerville Neighborhood Food Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $96
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
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.