Canalside Rail Trail Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to CA $4,200 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 Canalside Rail Trail Vacation Deals

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

Battery Wharf Hotel, Boston Waterfront

North End

Save 100% on your flight

CA $820

per person

Dec 2 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9/10 Wonderful! (2,041 reviews)

Loved it!

Reviewed on Oct 19, 2026

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

CA $1,792

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (458 reviews)

The Langham, Boston

Downtown Boston

Save 100% on your flight

CA $1,351

per person

Dec 2 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

Boston Harbor Hotel

North End

Save 100% on your flight

CA $1,675

per person

Dec 2 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

Amazing staff and property

Reviewed on Oct 18, 2026

Life House, Nantucket

Nantucket Town

Save 100% on your flight

CA $2,310

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

8.4/10 Very good! (76 reviews)

Ready to book your vacation to Canalside Rail Trail?

Choose your dates

Canalside Rail Trail Hotel Deals

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Fully refundableReserve now, pay when you stay

CA $146

CA $171 total

Nov 19 - Nov 20

includes taxes & fees

9.2/10 Wonderful! (2,086 reviews)

"Facilities were good. The rooms are dated"

Reviewed on Oct 18, 2026

Hotel UMass

1 Campus Center Way Amherst MA

9/10 Wonderful! (1,009 reviews)

"There is no protein option for breakfast. Milk might be the only choice. I personally don’t like to have carbs and anything sweet in the morning. If you are from Asia, American style breakfast might be a concern. Other than that, overall I enjoy my stay here. Perfect location to enjoy the foliage ..."

Reviewed on Oct 18, 2026

Get rates

Hotel Northampton

36 King Street Northampton MA

CA $210

CA $235 total

Oct 20 - Oct 21

includes taxes & fees

9.2/10 Wonderful! (1,005 reviews)

"Historic Hotel with an old tavern. Very comfortable bed & clean room. Check in & out went smoothly."

Reviewed on Oct 16, 2026

See all 313 properties in Montague

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.