Ossipee Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
Your Ossipee Vacation
With all your travel plans organized before you set off, our Ossipee vacation packages let you simply focus on vacationing! One place to base yourself in this interesting city is Chocorua Ski and Beach, which is good for camping and nature. You'll want to sightsee during your trip to Ossipee. Make time for big-name attractions such as Province Lake, Wentworth State Park and Sap House Meadery. Don't put off your visit to this city any longer. Your perfect Ossipee vacation is a couple of clicks away with Expedia.
Top Ossipee Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Price was CA $2,276, price is now CA $1,414 per person
CA $1,414
per person
May 16 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Classic luxury, a true five-star experience. Spectacular Boston Harbor views, top-notch staff, extra-comfortable bedding, rainfall shower.
Reviewed on Apr 12, 2026
The Langham, Boston
Downtown Boston
Price was CA $3,971, price is now CA $2,181 per person
CA $2,181
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The staff were so kind and let us check in early. They constantly asked how we were enjoying the stay and if there was anything that we needed. The property was clean and super cute!
Reviewed on Apr 13, 2026
Life House, Nantucket
Nantucket Town
Price was CA $4,613, price is now CA $2,846 per person
CA $2,846
per person
Jun 20 - Jun 27
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (65 reviews)
The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again.
Reviewed on Sep 26, 2025
The Ritz-Carlton, Boston
Downtown Boston
Price was CA $4,943, price is now CA $3,257 per person
CA $3,257
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (445 reviews)
Club level is well worth it. The service was wonderful
Reviewed on Apr 16, 2026
By the Sea Guests Bed & Breakfast & Suites
Price was CA $2,867, price is now CA $2,001 per person
CA $2,001
per person
Jun 20 - Jun 27
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!
Reviewed on Sep 20, 2025
Ossipee Hotel Deals
Mill Falls Resort Collection at the Lake
281 Daniel Webster Hwy Meredith NH
The price is CA $172 per night from May 4 to May 5
CA $172
CA $246 total
May 4 - May 5
includes taxes & fees
8.4/10 Very Good! (966 reviews)
Pool was open late which was nice, pool area could use an upgrade. When booking it said balcony but we didn't get that. Our window had the screen popped out and house keeping just came into the room at 8 a.m. the restaraunt was great and had a very friendly staff.
Reviewed on Apr 11, 2026
Best Western Plus Landmark Inn
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from May 10 to May 11
CA $151
CA $163 total
May 10 - May 11
includes taxes & fees
7.8/10 Good! (1,000 reviews)
The breakfast had expired yogurt but other then that it was great stay
Reviewed on Apr 13, 2026
Home2 Suites by Hilton North Conway
1439 White Mountain Hwy North Conway NH
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Apr 30 to May 1
CA $134
CA $145 total
Apr 30 - May 1
includes taxes & fees
9.4/10 Exceptional! (697 reviews)
This is a very clean hotel. Nice to have kitchen amenities in the room.
Reviewed on Apr 15, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
