Telegraph Hill Vacation Packages

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Top Holiday Package Deals in Telegraph Hill

Price found within the past 48 hours. Click for updated prices.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was CA $1,430, price is now CA $999 per person
CA $999
per person
Aug 17 - Aug 22
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.8/10 Good! (547 reviews)
Staff is welcoming and helpful. Breakfast was great every day, dining area well maintained. Rooms need some serious work, they are very outdated and poorly maintained, although clean enough. Bring your own pillow if you plan to stay, beds are uncomfortable. Back ache every morning. They are trying to improve the outside and there are fun activities with equipment provided.

Reviewed on Jun 7, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,492, price is now CA $1,497 per person
CA $1,497
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,000 reviews)
Un service 5 étoiles de l’arrivée au départ. Tout simplement exceptionnel.

Reviewed on Jun 12, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,961, price is now CA $1,225 per person
CA $1,225
per person
Aug 17 - Aug 22
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (187 reviews)
It’s a cute little place right on the ocean with its own beach.

Reviewed on Jun 12, 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Price was CA $2,536, price is now CA $1,700 per person
CA $1,700
per person
Aug 17 - Aug 22
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (701 reviews)
Charming, clean and great service

Reviewed on Jun 11, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,686, price is now CA $1,187 per person
CA $1,187
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Well located and very well maintained property.

Reviewed on Jun 11, 2026

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
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

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
The price is CA $267 per night from Jul 2 to Jul 3
CA $267
CA $368 total
Jul 2 - Jul 3
includes taxes & fees
9.2/10 Wonderful! (4,722 reviews)
"Very nice place. Sink didnt drain so they had to call maintenance and in the artist towers, the faucet is so close to the sink you can barely use it. Also on the last night even though the air was on 67 it stayed 74 in the room which made it hard to sleep"

Reviewed on Jun 13, 2026

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 $200 per night from Jul 5 to Jul 6
CA $200
CA $233 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (2,683 reviews)
"I went for work. Hotel is great. Rooms are very small (not a bad thing if you're a solo traveler) and the shared bathroom sounds weird at first but it's actually pretty neat of an experience. Overall, super clean, good location, well maintained, great staff. 10/10 will stay again when I go to ..."

Reviewed on Jun 13, 2026

The Revolution Hotel
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
The price is CA $327 per night from Jun 21 to Jun 22
CA $327
CA $438 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (5,108 reviews)
"The bed was super comfortable and it had a nice big showerhead with good pressure. Staff were very friendly and helpful. The only negative I have to say is that they put about $10 worth of chips, bottled water, cookies in the room and charge you $40 per day for it. It's not optional, the $40 charge ..."

Reviewed on Jun 13, 2026

The Godfrey Hotel Boston
See all 4,164 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.
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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 $999. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.