Downtown Boston Vacation Packages & Trips 2026 from CA $924

Top Holiday Package Deals in Downtown Boston

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

By the Sea Guests Bed & Breakfast & Suites

CA $924

per person

Sep 7 - Sep 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (193 reviews)

The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 2026

The Charles Hotel

West Cambridge

CA $1,328

per person

Aug 12 - Aug 16

found 21 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.4/10 Exceptional! (1,002 reviews)

Great experience but check in was delayed for a while and ended up in a different room category but hotel is beautiful and centrally located.

Reviewed on Jul 5, 2026

Four Seasons Hotel Boston

Bay Village

CA $2,537

per person

Sep 17 - Sep 20

found 18 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.4/10 Exceptional! (474 reviews)

perfecto

Reviewed on Jun 8, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

CA $3,971

per person

Sep 15 - Sep 22

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

10/10 Exceptional! (9 reviews)

I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

Chatham Tides

CA $2,240

per person

Aug 27 - Aug 30

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (720 reviews)

Chatham Tides is a slice of heaven. Beautiful location. Clean, well maintained. Staff was super helpful with local restaurants. My wife and I gave it a 11/10

Reviewed on Jul 2, 2026

Where to stay in Downtown Boston

Find the best Downtown Boston areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Boston

A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

4.5/5(274 area reviews)

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A tree-lined urban street with parked cars and benches.

Fenway–Kenmore

1 out of top 10 points of interest in this area

4.5/5(44 area reviews)

Home to Fenway Park and the Museum of Fine Arts, this vibrant area boasts numerous educational institutions, cultural attractions, and independent shops. Easily accessible via MBTA subway and bus lines, explore Kenmore Square and admire the iconic Citgo sign.

Downtown Boston Hotel Deals

Harborside Inn Of Boston

185 State St Boston MA

CA $318

CA $371 total

Jul 27 - Jul 28

includes taxes & fees

9.2/10 Wonderful! (6,784 reviews)

"Perfect location for our Boston trip"

Reviewed on Jul 6, 2026

The Langham, Boston

250 Franklin St Boston MA

Fully refundableReserve now, pay when you stay

CA $646

CA $752 total

Jul 31 - Aug 1

includes taxes & fees

9.6/10 Exceptional! (1,003 reviews)

"Simply excellent in all aspects."

Reviewed on Jul 2, 2026

The Dagny Boston

89 Broad Street Boston MA

Fully refundableReserve now, pay when you stay

CA $352

CA $460 total

Jul 26 - Jul 27

includes taxes & fees

9.6/10 Exceptional! (7,377 reviews)

"Lovely hotel in a very good location Downtown. Staff very helpful and friendly."

Reviewed on Jul 6, 2026

See all 4,146 properties in Downtown Boston

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

How much does a Downtown Boston vacation package cost?

We make it simple to travel somewhere new, with Downtown Boston packages starting from just CA $924. You'll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate escape, why not add a couple of tours and activities to your itinerary?

How do I get a cheap travel package to Downtown Boston?

Bundle, bundle, bundle. Flights, rental cars and hotels — combine whatever you need into a Downtown Boston vacation package to save tons of cash. Score even more bargains when you add extras such as sightseeing tours to your booking. But that's not the only good part. You have the flexibility to tailor your vacation your way. We offer over 550 air carriers and 1,000,000 hotels globally, so that everyone has a chance to travel and fulfill those vacation fantasies.

Where should I stay in Downtown Boston?

Urban adventurers come from far and wide to experience Fenway Park and TD Garden in Downtown Boston. Book a room near these terrific attractions and visit them whenever you please.

What are the top hotels in Downtown Boston?

Marriott Custom House One Bedroom Luxury Suite Located In Downtown Boston and Centralized Downtown Location | On are two of the most well-known hotels in Downtown Boston. Why not have a look at the amenities and rates at each and then decide?

How far in advance should I book my Downtown Boston vacation?

Smart travelers will likely want to book as early as possible. You can usually start comparing international fares on Expedia up to a year before your flight. If you've left things to the last minute, don't despair. Bargain prices sometimes occur just weeks before departure.

What does an Expedia Downtown Boston travel package include?

With Expedia, you can choose a combination of hotels, car rentals and flights to create your perfect Downtown Boston travel package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Remember, the more you bundle, the more you stand to save!

What should I know before booking a Downtown Boston travel package?

Bundling your bookings into a Downtown Boston vacation package is the easiest way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?

Can I choose my airline with a Downtown Boston Expedia vacation package?

Yes — that's one of the best things about an Expedia vacation package. You're in charge! We have access to more than 550 airline partners throughout the world, so you have lots of choice when planning your Downtown Boston escape.

If I'm not able to travel, can I cancel my Downtown Boston vacation package?

Because we know life is full of surprises, the answer is yes. For more information, head to our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it free of charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.