Waterboro Vacation Packages
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Your Waterboro Vacation
Build a custom vacation package to Waterboro and get ready to experience this exciting city the way you want. Consider spending some time in the neighborhood of South Sanford, which is great for walking and tons more. If taking in sights is on the agenda during your trip to Waterboro, visit top attractions like Little Ossipee Pond, Kennebunk Pond and Swan Pond. No matter your travel plans or budget, organizing your ultimate tailored Waterboro vacation is a walk in the park with Expedia.
Top Waterboro Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston
Price was CA $2,524, price is now CA $1,652 per person
CA $1,652
per person
Jun 16 - Jun 20
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
Boston Harbor Hotel
North End
Price was CA $2,778, price is now CA $1,697 per person
CA $1,697
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.
Reviewed on Mar 23, 2026
Fairmont Copley Plaza, Boston
Back Bay
Price was CA $3,393, price is now CA $2,277 per person
CA $2,277
per person
Jun 2 - Jun 7
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9/10 Wonderful! (1,196 reviews)
Great experience here, staff was fantastic, rooms were clean and comfortable.
Reviewed on Mar 23, 2026
The Colonnade Hotel Back Bay
Back Bay
Price was CA $2,972, price is now CA $2,007 per person
CA $2,007
per person
Jun 2 - Jun 7
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.2/10 Wonderful! (2,282 reviews)
Very good location, desk staff pleasant would definitely recommend
Reviewed on Mar 22, 2026
Cliff House Maine
Bald Head
Price was CA $4,313, price is now CA $2,919 per person
CA $2,919
per person
Jun 3 - Jun 8
found 1 hour ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
Check in was smooth and set the tone for a relaxed upscale experience. Valet available and doorman took our bags to the room. Room was great, beautiful ocean view, soft and silky sheets/down bedding. Pool and hot tub were amazing. Was so beautiful and peaceful hearing the waves crash against the rocks. Well worth it!
Reviewed on Mar 24, 2026
Waterboro Hotel Deals
DoubleTree by Hilton Hotel Portland
363 Maine Mall Rd South Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Apr 1 to Apr 2
CA $112
CA $122 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (1,371 reviews)
Good overall. I wished they had complimentary breakfast and wished they had a jacuzzi. Also, you have to walk through the bar and restaurant to get to the pool and gym which is a little awkward, but that can't be fixed without a remodel lol. Staff was very helpful and friendly
Reviewed on Mar 23, 2026
Tru by Hilton Portland Airport Area
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Apr 20 to Apr 21
CA $112
CA $122 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,760 reviews)
The property was clean the staff friendly. There's no microwave in the room and the gym is really small.
Reviewed on Mar 23, 2026
Long Creek Hotel by IHG
171 Philbrook Ave South Portland ME
Fully refundable
The price is CA $107 per night from Mar 30 to Mar 31
CA $107
CA $117 total
Mar 30 - Mar 31
includes taxes & fees
7.4/10 Good! (1,000 reviews)
Won’t return sludge in our bathroom. We had to use our towels over again because there was none! And house keeping had not come yet. We are talking 8 in the morning at this point!!
Reviewed on Mar 24, 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.
