
Canalside Rail Trail Vacation Packages
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Price found within the past 48 hours. Click for updated prices.

3.0-star property
The Cove at Yarmouth by Westgate Resorts
9.2/10 Wonderful! (254 reviews)
May 29 - Jun 3
5 night stay
Chicago (ORD) to Boston (BOS)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $959, price is now $592 per person
$592
per person
found 1 day ago
Nice property conveniently located, clean and with several pools and pickleball which we love! Drawbacks were the lack of elevators for hauling all of our luggage and supplies upstairs. Our unit also had a long steep staircase up to the primary (only) bedroom. People with mobility issues could struggle in this unit. There were bathrooms on both levels, which was nice. The unit has an efficiency kitchen for light meals/snacks and a small refrigerator. There is no laundry inside the unit but laundry is available in a public space. We enjoyed The Cove and the area.
Reviewed on Jun 5, 2025

5.0-star property
The Langham, Boston
Downtown Boston
9.6/10 Exceptional! (1,004 reviews)
Jun 16 - Jun 19
3 night stay
Chicago (CHI) to Boston (BOS)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,678, price is now $1,625 per person
$1,625
per person
found 1 day ago
No complaints , everything . I would go back again and again.
Reviewed on Jan 12, 2026

5.0-star property
Boston Harbor Hotel
North End
9.8/10 Exceptional! (1,001 reviews)
May 23 - May 25
2 night stay
Chicago (CHI) to Boston (BOS)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,356, price is now $857 per person
$857
per person
found 1 day ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.
Reviewed on Mar 24, 2024

4.0-star property
DoubleTree by Hilton Boston North Shore
8.2/10 Very Good! (2,398 reviews)
May 27 - Jun 3
7 night stay
Chicago (CHI) to Boston (BOS)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,743, price is now $1,111 per person
$1,111
per person
found 1 day ago
Beautiful hotel and loved my stay the only problem is the parking is a bit inconvenient
Reviewed on Dec 2, 2025

5.0-star property
Encore Boston Harbor
9.6/10 Exceptional! (3,612 reviews)
May 29 - Jun 3
5 night stay
Chicago (ORD) to Boston (BOS)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,584, price is now $1,138 per person
$1,138
per person
found 1 day ago
Consistently excellent rooms, restaurants, service and overall experience.
Reviewed on Feb 4, 2026
Top rated hotels for your Canalside Rail Trail vacation package

D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Free Cancellation
18.4 mi from city center
$134 nightly
The price is $149 total per night
$149 total
Mar 25 - Mar 26
Total with taxes and fees
D. Hotel Suites & Spa features a full-service spa, an indoor pool, and a gym. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and dry cleaning/laundry. Other amenities at this spa hotel include a sauna, a hot tub, and a 24-hour business center.
Pool
Hot Tub

Comfort Inn & Suites Hadley - Amherst
400 Russell St Hadley MA
Free Cancellation
12.03 mi from city center
$117 nightly
The price is $130 total per night
$130 total
Mar 29 - Mar 30
Total with taxes and fees
At Comfort Inn & Suites Hadley - Amherst, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to assist with luggage storage and securing valuables. Additional amenities include meeting rooms, a 24-hour business center, and free newspapers.
Pool
Breakfast included

Colonial Motel And Spa
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
23.72 mi from city center
$100 nightly
The price is $110 total per night
$110 total
Mar 24 - Mar 25
Total with taxes and fees
Guests of Colonial Motel And Spa have access to a full-service spa, 2 indoor pools, and a gym. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Other amenities at this spa motel include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
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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