Fenway–Kenmore Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Fenway–Kenmore

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $1,530, price is now CA $963 per person
CA $963
per person
Jan 29 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,397, price is now CA $1,548 per person
CA $1,548
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)
The best location and the beat service! The best swimming pool

Reviewed on Nov 9, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,234, price is now CA $1,488 per person
CA $1,488
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it.

Reviewed on Nov 8, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $1,789, price is now CA $1,298 per person
CA $1,298
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)
Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area.

Reviewed on Nov 7, 2026

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Price was CA $1,566, price is now CA $1,179 per person
CA $1,179
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (4,278 reviews)

Where to stay in Fenway–Kenmore

Find the best Fenway–Kenmore areas and neighborhoods for the activities you enjoy most. Learn more about Fenway–Kenmore
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

Fenway–Kenmore Hotel Deals

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 $164 per night from Nov 23 to Nov 24
CA $164
CA $191 total
Nov 23 - Nov 24
includes taxes & fees
citizenM Boston Back Bay
Hotel Commonwealth

Hotel Commonwealth

4.5 out of 5
500 Commonwealth Ave Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Nov 24 to Nov 25
CA $233
CA $338 total
Nov 24 - Nov 25
includes taxes & fees
Hotel Commonwealth
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
The price is CA $152 per night from Nov 22 to Nov 23
CA $152
CA $288 total
Nov 22 - Nov 23
includes taxes & fees
Hilton Boston Back Bay
See all 4,049 properties in Fenway–Kenmore
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 Fenway–Kenmore vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Fenway–Kenmore from just CA $963. And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to Fenway–Kenmore?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all. Select a combination that suits your style and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 hotels across the globe, which lets you customize your Fenway–Kenmore getaway.
Where should I stay in Fenway–Kenmore?
Most visitors to Fenway–Kenmore include both Fenway Park and TD Garden on their itineraries. Why not select a hotel near these popular attractions?
What are the top hotels in Fenway–Kenmore?
If this will be your first time in Fenway–Kenmore, lock in a room at New To Vrbo Sleek Boston Apt In Kenmore Square. 8min Walk To Fenway Park. Close To Universities or Hilton Boston Back Bay. Both hotels offer comfy beds and are top options with lots of travelers.
How far in advance should I book my Fenway–Kenmore vacation?
It's tricky picking the best time for airfares, but we generally say the earlier, the better. Plenty of international journeys on Expedia become available up to 12 months in advance. If you can't book early, don't worry. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Fenway–Kenmore travel package include?
Travel packages include hotels, flights and rental cars, but you can mix and match them to create your perfect Fenway–Kenmore getaway. You can also add on a few experiences and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Fenway–Kenmore travel package?
A package can be easier on the bank balance than individually booking everything you need for your escape. For example, bundle your flights, hotels and rental cars and save a pretty penny. Whatever your vacation plans, you'll find a package that suits your budget.
Can I choose my airline with a Fenway–Kenmore Expedia vacation package?
Yes — that's the beauty of an Expedia package. You get to decide. We have more than 550 airline partners all over the world, so you have options galore when organizing your Fenway–Kenmore escape.
If I'm not able to travel, can I cancel my Fenway–Kenmore vacation package?
Yes, you can. We get that life doesn't always go to plan, so we're happy to help if you have to make changes to your Fenway–Kenmore vacation package. You may be able to change or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Stay near popular Fenway–Kenmore attractions

A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

Fenway Park

9.2/10 (11,009 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
See properties

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.