Prospect Hill Vacation Packages

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Top Holiday Package Deals in Prospect Hill

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,379, price is now CA $901 per person
CA $901
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (189 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year

Reviewed on Jun 18, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,154, price is now CA $1,883 per person
CA $1,883
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,645, price is now CA $1,753 per person
CA $1,753
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (713 reviews)
Property is located on the beach, and that’s a huge plus. Rooms are clean, and the staff was pleasant to deal with. I met fellow travelers that book the same room on the same weeks for many years in a row, and that should tell you something.

Reviewed on Jun 23, 2026

Ashworth by the Sea

Ashworth by the Sea

3 out of 5
Hampton Beach
Price was CA $2,482, price is now CA $1,775 per person
CA $1,775
per person
Jul 26 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very good! (1,345 reviews)
Access and location to beach was great and staff was helpful. Elevator did not work, fridge in room would not get cold, water never turned hot and had to ask for refill for shampoo and conditioner.

Reviewed on Jun 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,204, price is now CA $1,603 per person
CA $1,603
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,015 reviews)
Expensive 2 star hotel. Stayed here twice and 2 star is the highest I could rate it. Not value for money. Trying to be something it is not and hiking the prices up for the World Cup is shameful. Tired dated and an average hotel

Reviewed on Jun 23, 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

Downtown Boston

4.5/5(197 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

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 $204 per night from Jun 30 to Jul 1
CA $204
CA $237 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (2,698 reviews)
"Clean room, friendly staff and a perfect location! There’s a 711 right across the street! 10/10!"

Reviewed on Jun 25, 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jul 2 to Jul 3
CA $215
CA $292 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (2,385 reviews)
"The front desk charged me for two night of overparking when I had a car only for one overnight parking. In addition, as I left the parking lot the machine charged me additional $18.00. The night I reported the one night overnight parking in the front desk, waited for about 25 minutes since frontdesk ..."

Reviewed on Jun 25, 2026

Hyatt Regency Boston/Cambridge
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 $228 per night from Jul 26 to Jul 27
CA $228
CA $314 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,475 reviews)
"3rd time in Boston, 3rd time staying here! It’s the only hotel in Boston I will book."

Reviewed on Jun 25, 2026

Seaport Hotel Boston
See all 4,134 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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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 $901. 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.

Stay near popular Prospect Hill attractions

Prospect Hill Park

8.2/5 (60 reviews)
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.
See properties

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $116
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
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.