Ashmont 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

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Top Holiday Package Deals in Ashmont

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

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,677, price is now CA $1,045 per person
CA $1,045
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (1,430 reviews)
The area is very good for walking and getting the sense of Boston. The rooms are clean and most importantly the staff is excellent.

Reviewed on May 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,076, price is now CA $1,888 per person
CA $1,888
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had

Reviewed on May 2, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $3,140, price is now CA $1,991 per person
CA $1,991
per person
Jul 25 - Aug 1
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (255 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $5,314, price is now CA $3,452 per person
CA $3,452
per person
Jul 25 - Jul 31
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Price was CA $2,414, price is now CA $1,576 per person
CA $1,576
per person
Jul 25 - Aug 1
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,009 reviews)
Clean room, helpful staff!

Reviewed on May 5, 2026

Where to stay in Ashmont

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

Ashmont Hotel Deals

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 $317 per night from May 25 to May 26
CA $317
CA $415 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (4,317 reviews)
A really nice place, in a great location with excellent staff

Reviewed on May 10, 2026

Seaport Hotel Boston
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 $173 per night from May 25 to May 26
CA $173
CA $202 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (2,608 reviews)
Very Lovely Place, Nice Architecture.

Reviewed on May 10, 2026

The Revolution Hotel
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 $283 per night from May 25 to May 26
CA $283
CA $386 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (4,655 reviews)
Clean Upscale And reasonably priced for Seaport. Nitpicking but wish it was an espresso machine instead of Keurig.

Reviewed on May 11, 2026

Omni Boston Hotel at the Seaport
See all 4,215 properties in Ashmont
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 an Ashmont vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Ashmont from just CA $1,045. And the more you bundle, the more you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Ashmont?
You'll save piles of cash if you bundle your car rentals, flights and hotels into an Ashmont travel package. Sometimes cheap means fewer options. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties all over the world, so you'll always have plenty of variety to choose from. Want to save even more? Add some popular activities to your package deal to unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Ashmont?
Travelers come from all corners of the globe to experience Fenway Park and TD Garden in Ashmont. Book a room near these awesome attractions and visit them whenever you please.
How far in advance should I book my Ashmont vacation?
Reserving your seat early with Expedia means one less thing to have to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. This is often the cheapest time to book. If circumstances have left you booking late, discount flights to Ashmont occasionally appear just a few weeks before departure.
What does an Expedia Ashmont travel package include?
Rental cars, hotels and flights — you'll find them all here. With Expedia, you can create your Ashmont travel package just how you like it. All you have to do is determine just what you need. Once you've made your booking, you can add extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking an Ashmont travel package?
When you book your hotels, flights and car rentals together, you'll walk away with awesome discounts. Whether you're planning an outdoor getaway in a chalet or want to stay in a ritzy city hotel, Expedia can help make it happen.
Can I choose my airline with an Ashmont Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Ashmont vacation package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Ashmont vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to find out more.

Discover the most popular places to visit in Ashmont

Fenway Park

Fenway Park

4.5/5(310 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University

Harvard University

4.5/5(284 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common

Boston Common

4.5/5(522 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $79
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 $116
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $47
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
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.