Telegraph Hill Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Telegraph Hill

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,931, price is now CA $816 per person
CA $816
per person
Dec 18 - Dec 23
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was CA $2,512, price is now CA $1,380 per person
CA $1,380
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was CA $1,647, price is now CA $1,034 per person
CA $1,034
per person
Dec 11 - Dec 13
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $2,646, price is now CA $1,736 per person
CA $1,736
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9/10 Wonderful! (1,354 reviews)
The Fairmont Gold level is the best I’ve ever experienced. From the way on line booking to the upgrade section, it was seamless. At check in, Kevin, got my room ready even though I was 6 hours early. Later that day, Kadija was accommodating to my request without any hesitation.

Reviewed on Oct 27, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,031, price is now CA $1,374 per person
CA $1,374
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Where to stay in Telegraph Hill

Find the best Telegraph Hill areas and neighborhoods for the activities you enjoy most. Learn more about Telegraph Hill
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

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

Telegraph Hill Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Nov 22 to Nov 23
CA $219
CA $312 total
Nov 22 - Nov 23
includes taxes & fees
Omni Boston Hotel at the Seaport
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 $150 per night from Nov 24 to Nov 25
CA $150
CA $174 total
Nov 24 - Nov 25
includes taxes & fees
9/10 Wonderful! (2,993 reviews)
"Hotel was in a good neighborhood, and close enough to walk to main attractions. Staff was attentive and helpful. Only caution...the rooms are small, if you get one with a bathroom inside the room (as opposed to group bathrooms down a hallway), the floor tends to flood after taking a shower. Lastly, ..."

Reviewed on Oct 28, 2026

The Revolution Hotel
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 $194 per night from Nov 29 to Nov 30
CA $194
CA $274 total
Nov 29 - Nov 30
includes taxes & fees
Seaport Hotel Boston
See all 4,127 properties in Telegraph 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 Telegraph Hill vacation package cost?
Cross off another part of the world with our Telegraph Hill vacation packages, which start from a low CA $816. Handpick the flights and hotels that match your travel plans. Then, add on a couple of enriching experiences to round off your unique adventure.
How do I get a cheap travel package to Telegraph Hill?
You'll save a pile of money if you bundle your hotels, car rentals and flights into a Telegraph Hill travel package. Sometimes cheap means fewer choices. But that's not the case with Expedia. We offer more than 550 airlines and 1,000,000 hotels across the globe, which means you'll always have plenty of options to choose from. Want to save even more? Add some exciting activities to your package deal and unlock even bigger bargains! After all, travel is about more than just getting to your destination.
Where should I stay in Telegraph Hill?
Make sightseeing a breeze by staying someplace close to Telegraph Hill's fantastic attractions. Fenway Park and TD Garden are two of the best in the area.
What are the top hotels in Telegraph Hill?
Whether you'll be staying for one night or longer in Telegraph Hill, you'll get a solid night's sleep at Spacious, Immaculate, Great Location. This option is a top pick for many travelers.
How far in advance should I book my Telegraph Hill vacation?
It can be hard to know when is the ideal time to book your Telegraph Hill trip. But typically the earlier you book, the better the prices. Sometimes, you can book your flights and hotels up to 12 months before departure. If you're considering a last-minute getaway, no need to stress! There are fabulous deals advertised on Expedia every day.
What does an Expedia Telegraph Hill travel package include?
Hotels, rental cars and flights, or any combination of the three — the choice is yours. Whether you're headed to Telegraph Hill with the family or traveling solo, there's a package to fit your style and budget. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a Telegraph Hill travel package?
Get set to save with an Expedia travel package. Combine your airfares, rental cars and hotels and enjoy exciting discounts. Hotels aren't your only option, however. Book with us and choose from island villas, cabins in the mountains and even glamping tents!
Can I choose my airline with a Telegraph Hill Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Simply choose the carrier you want and put together your ideal Telegraph Hill trip.
If I'm not able to travel, can I cancel my Telegraph Hill vacation package?
Certainly, and we're here to help. You may be able to cancel or amend your Telegraph Hill vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, take a look at our Customer Service Portal for more information.

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $69
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 $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $65
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
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.