Downtown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Holiday Package Deals in Downtown
Price found within the past 48 hours. Click for updated prices.
The Beverly
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (323 reviews)
Stopped in for overnight stay. Awkward check in as no emailed code (no desk staff on premises), got that worked out. Rooms are comfortable and appeared clean. Couple of places across street to eat and little shopping center, so nice options for quick stay.
Reviewed on Jul. 31, 2025
Encore Boston Harbor
per person
Sep 7 - Sep 10
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,159 reviews)
This was one of our best stays by far on our 30 day road trip in July. Our room was beautiful overlooking the Boston Harbor which was a romantic view at night. We deeply appreciated the convenience of the high-tech set up allowing us to control everything on an iPad. That was a unique experience and one I wish all hotels utilized. The bathtub is a great soaking tub with a TV on the wall and there’s even a place to rest your arms. The shower was nice too. The room was a large size compared to most hotel rooms.
Reviewed on Aug. 2, 2025
DoubleTree by Hilton Boston North Shore
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
The pool was closed. The first room we had before we switched was dirty. The room next us was screaming until 2am, and I tried calling the front desk but no one picked up.
And the room looked like it was decorated twenty years ago, and it was in the basement. It stank like a basement, a swimming pool, and an odd damp smell.
Reviewed on Jul. 31, 2025
Where to stay in Downtown
Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
West End
While West End might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like The Music Hall and Market Square.
Downtown Hotel Deals
Hampton Inn & Suites Portsmouth Downtown
23 Portwalk Pl, Portsmouth, NH
Fully refundableReserve now, pay when you stay
The price is CA $303 per night from Aug 25 to Aug 26
CA $303
CA $329 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Clean, friendly staff"
Reviewed on Aug. 1, 2025
Hilton Garden Inn Portsmouth Downtown
100 High St, Portsmouth, NH
Fully refundableReserve now, pay when you stay
The price is CA $291 per night from Aug 25 to Aug 26
CA $291
CA $316 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (70 reviews)
"Amazing food, great atmosphere"
Reviewed on Jul. 29, 2025
The Hotel Portsmouth
40 Court St., Portsmouth, NH
The price is CA $333 per night from Sep 1 to Sep 2
CA $333
CA $361 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
"Beautifully preserved old building Not enough light in bedroom"
Reviewed on Jul. 31, 2025
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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.