West Roxbury Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in West Roxbury

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 $1,447, price is now CA $924 per person
CA $924
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.4/10 Very Good! (1,441 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 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 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (255 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $6,452, price is now CA $4,123 per person
CA $4,123
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (419 reviews)
This is not a blow, your socks off property by any means! Dated and just ok. You’ll get the same thing for far less expense at a Sheraton, Hilton or Hyatt. Staff waa nice. There was nothing bad but certainly nothing spectacular or memorable to rave about.

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 1 day 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 1 day 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 West Roxbury

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

West Roxbury 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 $350 per night from May 25 to May 26
CA $350
CA $454 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (4,329 reviews)
Super clean! Nice heated pool! Amazing friendly staff from the valet, to concierge, to Tamo. Perfect location close to everything!

Reviewed on May 11, 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! (2,615 reviews)
This was such a fun location and a great way for people to share a room and save some money in downtown Boston. We loved the experience, the hotel, and the staff. 10/10. Would stay here again!

Reviewed on May 11, 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 $234 per night from May 29 to May 30
CA $234
CA $328 total
May 29 - May 30
includes taxes & fees
9.2/10 Wonderful! (4,661 reviews)
Great service, staff very helpful, and parking plus overnight stay are included.

Reviewed on May 11, 2026

Omni Boston Hotel at the Seaport
See all 4,045 properties in West Roxbury
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 West Roxbury vacation package cost?
Perhaps less than you might think — from as low as CA $924, in fact! By combining flights, hotels and car rentals into a tailor-made vacation package, your West Roxbury escape is just clicks away.
How do I get a cheap travel package to West Roxbury?
Search for flights that fit your busy schedule, add a hotel to your booking and watch the savings pile up with a West Roxbury vacation package. It's as easy as that! From flights and hotels to tours and rental cars, Expedia is where your cheap vacation begins. And with over 550 air carriers and 1,000,000 properties worldwide to select from, you won't be short of choice.
Where should I stay in West Roxbury?
A visit to West Roxbury isn't over until you've seen Fenway Park and TD Garden. Book a room close by for quick access to these fantastic attractions.
How far in advance should I book my West Roxbury vacation?
To bag cheap prices, book as soon as you can. Air carriers typically begin selling tickets, along with some of the lowest fares, up to a year in advance. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in West Roxbury, there are always lots of great deals on Expedia. Check them out now!
What does an Expedia West Roxbury travel package include?
Flights, hotels and rental cars — we have them covered. With Expedia, you can create your West Roxbury package the way you like it. All you have to do is work out exactly what you need. Once you've made your booking, you can add extras like activities and experiences. The more you bundle, the greater your savings!
Can I choose my airline with a West Roxbury Expedia vacation package?
Yes, you're in control. We have access to over 550 partner airlines all over the world, so you can customize your West Roxbury adventure according to your budget and travel needs.
If I'm not able to travel, can I cancel my West Roxbury vacation package?
Don't stress if you're rethinking your West Roxbury vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We understand life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in West Roxbury

Fenway Park

Fenway Park

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

Fenway Park
Harvard University

Harvard University

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

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.