Roslindale Vacation Packages
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Top Holiday Package Deals in Roslindale
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
CA $2,852
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
We weren't quite sure what to expect in a hotel in the heart of Boston but were extremely pleased with the experience and the room. The room/suite was a perfect size to relax in after a busy day seeing the sights of the city, and while our view was of the city and not the harbor, it was nonetheless wonderful. The room was appointed very tastefully and invited you to rest, The hotel and room had an air of quiet luxury which we did not expect. We very much enjoyed having breakfast by the dock/water and each time, the wait staff were so friendly and helpful. There is no question we will stay there again should our plans take us to Boston. Thanks helping to make our anniversary trip so great!
Reviewed on Aug 12, 2026
The Godfrey Hotel Boston
Downtown Boston
CA $1,841
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (5,158 reviews)
The property was convenient to everything. The accommodations were updated and clean. The staff were extremely attentive and professional. I would definitely stay there again.
Reviewed on Aug 12, 2026
Where to stay in Roslindale
Find the best Roslindale areas and neighborhoods for the activities you enjoy most. Learn more about Roslindale
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.
Back Bay
1 out of top 10 points of interest in this area
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.
Seaport District
1 out of top 10 points of interest in this area
Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.
Beacon Hill
1 out of top 10 points of interest in this area
Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.
North End
Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.
Roslindale Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
CA $263
CA $354 total
Aug 30 - Aug 31
includes taxes & fees
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
CA $327
CA $438 total
Aug 30 - Aug 31
includes taxes & fees
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
CA $190
CA $221 total
Aug 13 - Aug 14
includes taxes & fees
9/10 Wonderful! (2,826 reviews)
"A"
Reviewed on Aug 12, 2026
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 Roslindale vacation package cost?
Customize your Roslindale vacation package from a low CA $1,637. 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
The Square Root
The Square Root is just one of the places to see in Boston, so why not enjoy the other things to explore during your travels? Wander the forest or discover the area's sunsets.
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.
George Wright Golf Club
Enjoy a round of golf in Boston at George Wright Golf Club. Check out the churches and top-notch restaurants in this vibrant area.
Things to do
Boston Old Town Trolley Hop-on Hop-Off City Tour
CA $72
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
CA $118
per adult
92% of travellers recommend
View Boston Observation Deck Admission Tickets
CA $48
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.