Roslindale Vacation Packages

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Top Holiday Package Deals in Roslindale

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

Lakeside Inn

2 out of 5
Price was CA $918, price is now CA $586 per person
CA $586
per person
Oct 28 - Nov 1
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,174 reviews)
nice stay, liked the room and bed, breakfast could have been better,

Reviewed on Aug. 23, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,905, price is now CA $1,672 per person
CA $1,672
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug. 24, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,866, price is now CA $1,145 per person
CA $1,145
per person
Nov 3 - Nov 10
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Great Experience at a great location

Reviewed on Aug. 21, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,835, price is now CA $1,808 per person
CA $1,808
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $1,801, price is now CA $1,233 per person
CA $1,233
per person
Oct 28 - Nov 1
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (585 reviews)
The location was great and we were able to get to all the sites easily. Also, liked having two beds and two bathrooms for the price. However, everything was very cheap in there. The sheets were nubbie because they were cheap and worn. The toliet paper was so awful we had to buy our own. The beds had little support. The place was clean though. So if you don't care much about the bed, sheets, and toliet paper it is a good pick. If you do maybe pick somewhere else.

Reviewed on Aug. 17, 2025

Where to stay in Roslindale

Find the best Roslindale areas and neighborhoods for the activities you enjoy most. Learn more about Roslindale
Downtown Boston showing a city and night scenes as well as a small group of people

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

Roslindale 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 $204 per night from Sep 1 to Sep 2
CA $204
CA $244 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (3,276 reviews)
"Clean comfortable room with massive comfy bed. Very conveniently situated for the cruise port. Staff were extremely professional, friendly and helpful."

Reviewed on Aug. 25, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Sep 1 to Sep 2
CA $263
CA $363 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (3,870 reviews)
"We stayed for a couple of days at the end of our trip to Boston, the hotel was perfect for relaxing by the pool and a short walk from all the areas we wanted to see whilst visiting."

Reviewed on Aug. 25, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is CA $269 per night from Sep 1 to Sep 2
CA $269
CA $313 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (3,692 reviews)
"Decor and furnishings unique. Refreshing and different. View from lounge area of Boston skyline is amazing!"

Reviewed on Aug. 24, 2025

citizenM Boston North Station
See all 3,650 properties in Roslindale
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 Roslindale vacation package cost?
Customize your Roslindale vacation package from a low CA $586. Choose from any combination of rental cars, flights and hotels to put together the trip you've been dreaming of. Be sure to add on some activities and experiences!
How do I get a cheap travel package to Roslindale?
Combine your flights and hotels, add extras such as activities or a rental car, and save with a Roslindale vacation package. You won't just score awesome discounts on your trip — you'll have plenty of choice too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 properties around the globe. Your next big adventure starts right here, right now!
Where should I stay in Roslindale?
A visit to Roslindale isn't complete until you've seen Fenway Park and TD Garden. Stay within walking distance for easy access to these popular sights.
What are the top hotels in Roslindale?
Modern Style Cozy Private Apt is one of Roslindale's most popular hotels. Book a room here and you can rest easy knowing you're in capable hands.
How far in advance should I book my Roslindale vacation?
Your safest bet is to book early. Air carriers usually release flight tickets around a year in advance, and this is an ideal opportunity to score some of the cheapest prices. Just been told you should take all your vacation days in a few weeks? Don't fret. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Roslindale travel package include?
That depends on what you're looking for. If you're traveling by yourself, you might decide to combine hotels and flights. Taking the whole crew to Roslindale? A travel package including hotels, rental cars and flights might be a better fit. Expedia gives you the freedom to build your own travel package.
What should I know before booking a Roslindale travel package?
You can save a tidy sum by bundling your airfares, hotels and rental cars. Once you've created your package, you can add on tours and activities. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Roslindale Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from around the world. With so many choices, finding the right carrier to get you to Roslindale will be a cinch.
If I'm not able to travel, can I cancel my Roslindale vacation package?
We totally get it — life doesn't always go according to plan. If you've locked in a Roslindale vacation package and need to cancel or amend it, we can help. We suggest checking out our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $109
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $97
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

CA $47
per adult
84% 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.