Roslindale Holidays from £1,422

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

Your Roslindale Holiday

Make planning your travels easy by booking a holiday package to Roslindale. We'll take care of the details, so you can focus on savouring everything this neighbourhood can offer. Begin your trip to Roslindale by heading to nearby attractions such as Franklin Park Zoo, Samuel Adams Brewery and Larz Anderson Auto Museum. Expedia will help you turn your ideal Roslindale holiday into reality, no matter your budget or travel plans.

Price found within the past 48 hours. Click for updated prices.
Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

3 out of 5
South End
Save 100% on your flight
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.8/10 Excellent! (968 reviews)
Worked out really well from 3 days in Boston

Reviewed on 6 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on 3 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9/10 Wonderful! (2,679 reviews)
We Ubered to Club Q from the airport, an easy ride to the financial district and just down the street from Faneuil Hall and Quincy Market. The Elephant Castle Pub next-door had great food. The hotel staff was absolutely amazing. Our room was clean and bed was comfortable. We were quite pleased with our stay.

Reviewed on 8 Aug 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
11 Oct - 18 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8/10 Very Good! (571 reviews)
Washer/Dryer did not work properly. Despite 2 calls and 1 email to customer service, the issue was not resolved. The washer didn’t rinse clothing out and they remained sopping wet. They required extensive drying time as a result ( over 4 hours). This was extremely inconvenient.

Reviewed on 2 Aug 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 which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Roslindale

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 £189 per night from 24 Aug to 25 Aug
£189
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,784 reviews)
Decent Size Studio Rm, can get noisy from planes
"I stayed at the Artist Studio Tower, which faces the East and North I think. The room itself was thoughtfully designed to utilize limited space for comfort, and looked nice and luxurious. However, there wasn't any dedicated desk for working on a laptop (Just a small stand for a coffee machine and ..."

Reviewed on 7 Aug 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £169 per night from 1 Sept to 2 Sept
£169
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (3,206 reviews)
Wonderfully Stay
"We thoroughly enjoyed our stay! The staff was friendly, so very helpful in what we asked, was just a wonderful experience!"

Reviewed on 5 Aug 2025

Hilton Boston Park Plaza
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £165 per night from 10 Aug to 11 Aug
£165
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,553 reviews)
"Only con which in my opinion isn’t truly a con is the rooms are small. Get the window upgrade totally worth it. Other then a small room everything is else is outstanding. Comfortable bed, easy check in and check out, everything can be done from provided iPad, common areas are wonderful!. Excellent ..."

Reviewed on 4 Aug 2025

citizenM Boston Back Bay
See all 3,634 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

Why should I book my Roslindale holiday with Expedia?
Expedia has you covered for all aspects of your upcoming Roslindale getaway. You'll always get the best deal possible, but when you bundle your accommodation, flights and/or hire car into a holiday package, you'll score even more savings. Keen to really make the most of your break? Add some exciting tours and activities to your package. We offer flexible cancellation policies on almost all bookings, so you won't need to worry if your plans change. Head over to our Customer Service Portal link to learn more.
What are the top hotels for my holiday in Roslindale?
If it's comfort and convenience you're seeking, book a room at Modern Style Cosy Private Apt. Spend your evenings unwinding here and your days exploring Roslindale's best attractions.
How do I get a cheap holiday to Roslindale?
Secure flights that suit your schedule, add a hotel to your booking and watch how much you save with a Roslindale holiday. It's that easy! From flights and hotels to hire cars and activities, Expedia makes travelling cheap and easy. And with more than 400 air carriers and 321,000 hotels throughout the world to select from, you won't be short of choice. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Roslindale holiday?
Make sure your next holiday in Roslindale is one to remember by stopping by its leading attractions. Fenway Park, TD Garden, Boston Common and Boston Convention and Exhibition Centre are just a few of the things to put on your itinerary while you're in the city.
What is the best area to stay in when on holiday in Roslindale?
Roslindale has lots of popular places to discover, such as Forest Hills Cemetery. Book accommodation near this attraction and make sightseeing hassle-free.
Do I need a visa for my Roslindale holiday?
Visa requirements for Roslindale vary based on your nationality and the purpose of your visit. It's wise to check official government websites to determine if you need a visa for your holiday. Here you'll also find the most up-to-date information, including details about application procedures and any supporting documentation that may be necessary. Research your visa requirements well in advance to ensure a hassle-free travel experience. Finally, make sure your passport is valid for a further six months from your planned date of return.
What should I wear on my Roslindale holiday?
Do some research into the sorts of clothing people in Roslindale wear, and maybe even check out fashion pages on social media for inspiration. Try to create a versatile wardrobe with pieces that work for your destination and show off your unique sense of style.
What does an Expedia Roslindale holiday include?
With Expedia, you can choose any combination of flights, hotels and car hires to build your perfect Roslindale travel package. Once you've made your booking, simply add on the fun things like tours and activities. Don't forget, the more you bundle, the greater the savings! Explore all kinds of styles on Expedia and find the perfect fit for you and your crew. From the most popular property types, like apartments and private holiday homes, to many other options, there are loads of holiday escapes in Roslindale to select from so you can personalise your stay just the way you like it.
Does Expedia offer Book Now, Pay Later Roslindale holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your hip pocket. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more money to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna offers payments in multiple transactions that suit all budgets, so you can jet away on that well-deserved holiday now.
  • No-deposit holidays: Clicking on the "book now" button is easier with this payment option. With no deposit required for your escape, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Roslindale Expedia holiday?
Yes — that's one of the best things about an Expedia holiday package. You're the boss! We have access to more than 400 airline partners around the world, so you have lots of choice when putting together your Roslindale adventure.

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£59
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£52
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

£25
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. Flight-inclusive packages are ATOL protected.