Portland Adventure Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Adventure hotel deals in Portland
Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Collection
Price was CA $5,398, price is now CA $4,844 per person
CA $4,844
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (114 reviews)
The White Barn Inn was first class from check in to check out! It has the wow factor we love - complimentary valet parking, welcome cocktails, basket of treats waiting in our room, coffee & pastry delivered to our door at our preferred time each morning, turn down service, incredible staff, delicious restaurant, and perfect location. We will definitely return!
Reviewed on May 12, 2026
The Westin Portland Harborview
Downtown Portland
Price was CA $1,780, price is now CA $1,735 per person
CA $1,735
per person
Jun 17 - Jun 21
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,002 reviews)
Parking garage right next to hotel, close to restaurants, old port and music venues.
Reviewed on Apr 29, 2026
Kennebunkport Captains Collection
Price was CA $1,298, price is now CA $1,267 per person
CA $1,267
per person
Jul 7 - Jul 9
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (699 reviews)
We absolutely loved our stay! Everything was clean, the staff were super helpful and friendly, and breakfast was great. This was a nice stop after a long day of traveling, and a great place to relax. We can’t wait to come back!
Reviewed on May 8, 2026
5* Adventure holidays in Portland
Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Collection
Price was CA $5,398, price is now CA $4,844 per person
CA $4,844
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (114 reviews)
The White Barn Inn was first class from check in to check out! It has the wow factor we love - complimentary valet parking, welcome cocktails, basket of treats waiting in our room, coffee & pastry delivered to our door at our preferred time each morning, turn down service, incredible staff, delicious restaurant, and perfect location. We will definitely return!
Reviewed on May 12, 2026
3 Night Adventure holidays in Portland
Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview
Downtown Portland
Price was CA $1,085, price is now CA $1,080 per person
CA $1,080
per person
Jun 20 - Jun 23
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,002 reviews)
Parking garage right next to hotel, close to restaurants, old port and music venues.
Reviewed on Apr 29, 2026
Kennebunkport Captains Collection
Price was CA $1,298, price is now CA $1,267 per person
CA $1,267
per person
Jul 7 - Jul 9
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (699 reviews)
We absolutely loved our stay! Everything was clean, the staff were super helpful and friendly, and breakfast was great. This was a nice stop after a long day of traveling, and a great place to relax. We can’t wait to come back!
Reviewed on May 8, 2026
4 Night Adventure holidays in Portland
Price found within the past 48 hours. Click for updated prices.
Comfort Inn South Portland Airport
Price was CA $1,290, price is now CA $1,218 per person
CA $1,218
per person
Jun 17 - Jun 21
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (2,030 reviews)
Bathroom door would rub on the floor and was very tight between toilet and door.
At least the sink was outside of bathroom.
Reviewed on May 11, 2026
Hampton Inn Portland Downtown - Waterfront
Downtown Portland
Price was CA $2,114, price is now CA $1,903 per person
CA $1,903
per person
Jun 17 - Jun 21
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,007 reviews)
Very dirty windows, no business center where we could use a computer to print boarding passes. Dirty tables after breakfast so we cleaned them ourselves.
Reviewed on May 11, 2026
Hilton Garden Inn Portland Downtown Waterfront
Downtown Portland
Price was CA $2,553, price is now CA $2,408 per person
CA $2,408
per person
Jun 17 - Jun 21
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Really nice room. The property was great. $40 parking was over priced.
Reviewed on May 12, 2026
Adventure Hotels in Portland
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
9.4/10 Exceptional! (1,648 reviews)
Very nice hotel with a wonderful staff. Also, in a prime location that allowed us to walk to everything we did.
Reviewed on May 11, 2026
Nonantum Resort
95 Ocean Ave Kennebunkport ME
Stay at this hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.2/10 Wonderful! (878 reviews)
Room was clean but bathroom sink full of rust disappointing. Staff was very helpful and accommodating. Breakfast was good but our stay coincided with Mother’s Day brunch and communication was unclear of when guest should arrive so that was disappointing.
Reviewed on May 10, 2026
The Westin Portland Harborview
157 High St Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,005 reviews)
Parking garage right next to hotel, close to restaurants, old port and music venues.
Reviewed on Apr 29, 2026
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
