Hillside Vacation Packages
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Top Hillside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kennebunkport Captains Collection
Price was CA $1,436, price is now CA $1,245 per person
CA $1,245
per person
Jun 5 - Jun 7
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (692 reviews)
Historic, cozy, and charming mansions and rooms...our stay was amazing.
Reviewed on Mar 15, 2026
1802 House Bed and Breakfast
Price was CA $1,158, price is now CA $1,024 per person
CA $1,024
per person
Jun 5 - Jun 7
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (104 reviews)
Great place to stay for a getaway. Breakfast is outstanding, hostess and her husband prepare fresh ingredients with three tasty courses.
Rooms are well decorated, clean, bright and comfortable. We stayed there in 2001 and again in 2025. Our favorite in Kennebunk Port.
Reviewed on Oct 28, 2025
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,153, price is now CA $1,913 per person
CA $1,913
per person
May 29 - May 31
found 4 hours ago
Roundtrip flight included
Toronto (YTZ) to Portland (PWM)
9.6/10 Exceptional! (179 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $1,619, price is now CA $1,441 per person
CA $1,441
per person
Jun 5 - Jun 7
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (296 reviews)
We thoroughly enjoyed our 4-night stay at The Docent's Collection. The staff was outstanding (shout-out to Spencer and Sarah!). The apartment we stayed in was roomy, impeccably clean, and well-furnished. We had everything we needed for our stay. Security was great, parking was easy, and right next to a police parking lot, so very secure. We look forward to staying here again!
Reviewed on Apr 15, 2026
Hillside Hotel Deals
Dormir
965 Roosevelt Trail Windham ME
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Apr 26 to Apr 27
CA $191
CA $208 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Parking was convenient. Room was clean and comfortable
Reviewed on Apr 19, 2026
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from May 7 to May 8
CA $165
CA $180 total
May 7 - May 8
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
The casino was not lively and barely had any tables open except for blackjack. We did not have breakfast while there.
Reviewed on Apr 21, 2026
Hampton Inn Oxford
151 Main St Oxford ME
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from May 7 to May 8
CA $152
CA $165 total
May 7 - May 8
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
The room was nice. Easy check in and out.
Reviewed on Apr 10, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
