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.
The Langham, Boston
Downtown Boston
Price was CA $3,131, price is now CA $2,062 per person
CA $2,062
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
We loved our stay here. The restaurant "The Fed" had cozy decor, amazing food and served food until 10:30pm. This was great when our flight in was delayed and we could still eat dinner when we arrived. The rooms have lots of lighting choices, bed side reading lights too, and little trays to place your odds and ends to help keep organized. We could have used a few more hangers, but the hotel staff continuously gave us water for the room, and there were cozy robes and slippers there too. When housekeeping came they tidied everything up nicely, even rolling up our laptop cords. The staff was friendly and helpful with everything from maps and directions to concierge and luggage hold the day we were to depart. Also love the twelve pm checkout. A lovely place to stay. We were out our few days visit from 9am to 9pm each day and it really was such a wonderful place to return to each night.
Reviewed on Apr 21, 2026
The Highliner Hotel
Downtown Gloucester
Price was CA $4,005, price is now CA $2,701 per person
CA $2,701
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
10/10 Exceptional! (2 reviews)
Digital check in process was easy to do on my phone. The staff was helpful, it wasnt just automated. The building location was perfect for us to explore the town on foot. Parking was tricky, but they detailed your parking options well. Many food options nearvy. Good night life options even in off season. The building and room were immaculate with a luxery feeling. Music in the hallways, fresh paint, umbrellas by the door, free water station. There was green mountain coffee pods, not the usual hotel mud coffee. 15$ voucher to a nearby cafe was enough for two bagels and two small coffees. Overall, this place was amazing!
Reviewed on Apr 19, 2026
The Mansion at Ocean Edge
Price was CA $4,410, price is now CA $3,018 per person
CA $3,018
per person
Jul 5 - Jul 11
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (1,001 reviews)
Unfortunately, we went during the slow season. They don't open fully until May 1st. The bar wasn't open until 5pm and restaurants were not open. Pool was closed. No chairs on the deck. Everything was covered. Property was nice. Just would have been nice to have a few options.
Reviewed on Apr 24, 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
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.
Telegraph Hill Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from May 3 to May 4
CA $231
CA $316 total
May 3 - May 4
includes taxes & fees
9.6/10 Exceptional! (4,217 reviews)
Absolutely outstanding
Reviewed on Apr 25, 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from May 10 to May 11
CA $239
CA $335 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (4,592 reviews)
Exceptional sty all-around
Reviewed on Apr 25, 2026
Harborside Inn Of Boston
185 State St Boston MA
The price is CA $257 per night from May 3 to May 4
CA $257
CA $299 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (6,488 reviews)
Perfect area
Reviewed on Apr 25, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Telegraph Hill
Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Gillette Stadium
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's great live music and acclaimed theater scene.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $79
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $47
per adult
88% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $116
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.