Observatory 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 Observatory 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
per person
Aug 25 - Aug 29
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Staff was excellent. Room was clean and spacious but, there was no ventilation in the bathroom. That really sucked...

Reviewed on Jul. 24, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 1 - Sep 4
found 23 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on Jul. 23, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
per person
Oct 11 - Oct 15
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.2/10 Wonderful! (1,087 reviews)
The property is conveniently located to the major roads and is in walkable distance to the main historical landmarks.

Reviewed on Jul. 24, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
Oct 11 - Oct 15
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8/10 Very Good! (566 reviews)
Good location. Walkable to activities and shops and restaurants. The place is nice and clean but the communication with the customer service team was not easy.

Reviewed on Jul. 24, 2025

The Boxer

The Boxer

4 out of 5
West End
per person
Sep 1 - Sep 4
found 23 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Boston (BOS)
8.6/10 Excellent! (1,236 reviews)
This hotel is super cute. Our room was pretty tiny but the proximity to the TD Garden is what makes this the real winner. If you are super sensitive to noise the water running through the pipes is quite loud. It never woke me up but it was annoying when we were relaxing in our room. As far as noise goes, we never heard anyone in the hallway.

Reviewed on Jul. 22, 2025

Where to stay in Observatory Hill

Find the best Observatory Hill areas and neighborhoods for the activities you enjoy most. Learn more about Observatory 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

Observatory Hill Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
The price is CA $250 per night from Aug 24 to Aug 25
CA $250
CA $347 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,716 reviews)
"This property is in a perfect location in the Seaport. We loved it!"

Reviewed on Jul. 24, 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 $258 per night from Aug 10 to Aug 11
CA $258
CA $300 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,487 reviews)
"Great place. Just be prepared that there is no curb drop off or hotel parking, so figure out how you are going to park and get your suitcases there ahead of time. Very modern, good restaurant/coffee bar and large hangout lobby, 10 min walk to Finway area. Highly recommend."

Reviewed on Jul. 23, 2025

citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Aug 24 to Aug 25
CA $237
CA $276 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (3,578 reviews)
"It was wicked awesome"

Reviewed on Jul. 24, 2025

citizenM Boston North Station
See all 3,691 properties in Observatory 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 an Observatory Hill vacation package cost?
Get ready to book, because a getaway to Observatory Hill starts from an enticing CA $387. When you combine your hotels, flights and car rentals into a vacation package, you'll pick up the best prices.
How do I get a cheap travel package to Observatory Hill?
One word: bundle. Hotels, flights and rental cars — combine whatever you need into an Observatory Hill vacation package to save a pile of cash. Score even more bargains when you add extras such as activities or tours to your booking. But that's not the only impressive part. You have the freedom to put together your trip your way. We offer over 550 airlines and 1,000,000 properties in all corners of the globe, so that everyone has an opportunity to travel and live out those vacation fantasies.
Where should I stay in Observatory Hill?
Make sightseeing a breeze by staying someplace just a stone's throw away from Observatory Hill's fantastic attractions. Harvard Square and Massachusetts Institute of Technology are two visitor favorites.
What are the top hotels in Observatory Hill?
Get your escape off to a fantastic start by reserving a room at Luxury Harvard/mit Victorian. It's one of most popular hotels in Observatory Hill. Another option is Charming Harvard Victorian With Pkng.
How far in advance should I book my Observatory Hill vacation?
To bag discount prices, book as soon as you can. Airlines usually start selling tickets, along with some of the lowest fares, up to a year in advance. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you've decided on a last-minute getaway to Observatory Hill, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Observatory Hill travel package include?
Hotels, rental cars and flights, or any combination of them — you decide! Whether you're exploring Observatory Hill with the whole family or enjoying a solo break, there's a bundle to match every style and budget. Once you've made your booking, why not add on some tours and experiences?
What should I know before booking an Observatory Hill travel package?
Whether it's adventure or relaxation you're craving, an Observatory Hill vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with an Observatory Hill Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Just choose the carrier that suits you and create the perfect Observatory Hill escape.
If I'm not able to travel, can I cancel my Observatory Hill vacation package?
Don't stress if you're rethinking your Observatory Hill vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We realize life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.

Discover the most popular places to visit in Observatory Hill

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common which includes flowers, a garden and landscape views

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

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
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $46
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
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.