Roslindale Vacation Packages

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  • 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 Roslindale

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

Good Hotels Boston

2 out of 5
South End
Price was CA $1,489, price is now CA $986 per person
CA $986
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,291, price is now CA $1,383 per person
CA $1,383
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Price was CA $2,048, price is now CA $1,451 per person
CA $1,451
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Boston (BOS)
8.6/10 Excellent! (467 reviews)
I love the design of the hotel! The pods are really spacious and provide a lot of privacy. This is my second stay here and will always return when I’m back in Boston!

Reviewed on Jun 21, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was CA $1,406, price is now CA $1,032 per person
CA $1,032
per person
Sep 3 - Sep 7
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (189 reviews)
Nice property. A little parking issue due to limited parking. Only one space per room, I think some people didn't listen. But breakfast, the private beach, the staff, the amenities all awesome.

Reviewed on Jun 25, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $2,722, price is now CA $2,012 per person
CA $2,012
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (428 reviews)
The valet was fast and professional, the room was clean, the staff are very helpful. I would definitely stay again!

Reviewed on May 25, 2026

Where to stay in Roslindale

Find the best Roslindale areas and neighborhoods for the activities you enjoy most. Learn more about Roslindale
A nighttime street scene with illuminated trees, a market stall, and historic buildings.

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

Roslindale Hotel Deals

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 $203 per night from Jul 1 to Jul 2
CA $203
CA $237 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (2,699 reviews)
"Interesting , unique hotel in a nice neighborhood"

Reviewed on Jun 26, 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
The price is CA $237 per night from Jul 1 to Jul 2
CA $237
CA $318 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (2,388 reviews)
"Staff was amazing! View from our balcony was amazing!!"

Reviewed on Jun 25, 2026

Hyatt Regency Boston/Cambridge
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 $268 per night from Jul 5 to Jul 6
CA $268
CA $361 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (4,473 reviews)
"Conveniently located, excellent service"

Reviewed on Jun 26, 2026

Seaport Hotel Boston
See all 4,100 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 $986. 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.

Stay near popular Roslindale attractions

Boston Nature Center and Wildlife Sanctuary

Enjoy an outing to Boston Nature Center and Wildlife Sanctuary during your stay in Boston. Discover the top-notch restaurants and fascinating museums in this vibrant area.
See properties

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
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
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
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.