Ossipee Vacations from $820

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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.

The Latest Ossipee vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was $1,245, price is now $820 per person
$820
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
8.4/10 Very Good! (1,451 reviews)
For the money, can non go wrong with this choice

Reviewed on May 23, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,065, price is now $1,218 per person
$1,218
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This was 10/10 with everything top tier

Reviewed on May 20, 2026

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,714, price is now $1,808 per person
$1,808
per person
Jul 27 - Aug 1
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Boston (BOS)
8/10 Very Good! (276 reviews)
There was no housekeeping to clean my house the next day we have to request amenity for my stay.

Reviewed on May 19, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $1,554, price is now $1,036 per person
$1,036
per person
Jul 6 - Jul 10
just found
Roundtrip flight included
Dallas (DFW) 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

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was $1,425, price is now $951 per person
$951
per person
Aug 4 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Boston (BOS)
8.6/10 Excellent! (414 reviews)
Great access very cheep. Was not expecting that much for a reasonable price, but was surprised when they had a 24h autolock, well furnished and clean bunkers, and most importantly, well mannerred room mates. Also had a small snack stand, free coffee in the morning which made me very happy. would love to stay here again!

Reviewed on May 18, 2026

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Ossipee Hotel Deals

Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy Meredith NH
$137 nightly
The price is $149 total per night from May 31 to Jun 1
$149 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (988 reviews)
"Our room has a great view and was just lovely"

Reviewed on May 21, 2026

Mill Falls Resort Collection at the Lake
The Green Granite North Conway, an Ascend Collection Hotel

The Green Granite North Conway, an Ascend Collection Hotel

2.5 out of 5
1515 White Mountain Hwy North Conway NH
Fully refundable
$72 nightly
The price is $78 total per night from May 31 to Jun 1
$78 total
May 31 - Jun 1
Total with taxes and fees
6.6/10 (1,228 reviews)
"Yes, to both"

Reviewed on May 20, 2026

The Green Granite North Conway, an Ascend Collection Hotel
Home2 Suites by Hilton North Conway

Home2 Suites by Hilton North Conway

3 out of 5
1439 White Mountain Hwy North Conway NH
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $115 total per night from Jun 9 to Jun 10
$115 total
Jun 9 - Jun 10
Total with taxes and fees
9.4/10 Exceptional! (719 reviews)
"Booked a room with handicap accessible bathroom. Unfortunately tub/shower was unusable as tub bottom was extremely slippery as was bathroom floor. But it was a short trip from your vehicle to your room. Take elevator inside the lobby and when the door opened upstairs your room was in sight. Also ..."

Reviewed on May 21, 2026

Home2 Suites by Hilton North Conway
See all 2,075 properties in Ossipee
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.

Find the Best Ossipee Vacation Packages

Ossipee Essential Information

Language
English
Currency
U.S dollars
Population
4,700
Top Sights
Allen Albee Beach, Brewster Beach and Wolfeboro Abenaki Ski Area

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Frequently asked questions

How much does an Ossipee vacation package cost?
You can grab a vacation package to this destination from $820 on Expedia. But how much your vacation to Ossipee costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Ossipee?
If you're looking to snag a cheap Ossipee vacation package, consider traveling in October, November and December. You'll usually find lower prices on flights and accommodations during these months — perfect for a budget-friendly break.
How many days is enough for Ossipee?
With a well-planned itinerary, you can easily tick off the main Ossipee sights in a few days. But if you'd like to discover lesser-known spots or go on day tours, think about booking your Ossipee vacation for longer.
How to find the best Ossipee package deals?
Use Expedia's handy filters to help you find some unbeatable Ossipee package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Ossipee package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book an Ossipee vacation as a package?
You can enjoy significant savings on your Ossipee retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Ossipee?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Ossipee escape.
Does Expedia offer Book Now, Pay Later Ossipee vacation packages?
Your Ossipee break is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.