Ossipee Vacations from $425

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Ossipee Vacation

With all your travel plans worked out before you go, our Ossipee vacation packages mean you can focus more on vacationing! One neighborhood to base yourself in this fascinating city is Chocorua Ski and Beach, which is great for camping and nature. If a sightseeing tour is part of the plan during your trip to Ossipee, visit top attractions like Province Lake, Sap House Meadery and Wentworth State Park. Don't put off visiting this city any longer. The perfect Ossipee vacation is a few quick clicks away with Expedia.

The Latest Ossipee Vacation Packages

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

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 24 - Aug 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Great hotel. Very accommodating!

Reviewed on Jun 6, 2024

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
per person
Jul 24 - Jul 28
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
10/10 Exceptional! (3 reviews)
Everything was perfect

Reviewed on May 28, 2024

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
7.4/10 Good! (189 reviews)
The grounds are well kept. The staff are very friendly and helpful. The building itself is tired. The kitchenette had no utensils and only paper cups. Also the hot plate didn’t have a place to plug in. The fridge and microwave worked though and that’s all we needed. Just a heads up in case you need more. They had a variety of breakfast options that are included. Pancakes, waffles, eggs, muffins etc. For the price, we were happy.

Reviewed on Jun 3, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (275 reviews)
This is a beautiful hotel with a great gym and first class service. The housekeeping team is world class.

Reviewed on Jun 5, 2024

La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
Assembly Square
Save 100% on your flight
per person
Aug 22 - Aug 26
found 22 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
7.4/10 Good! (1,944 reviews)
Perfect for what I needed. Close to Assembly Row. East walk. Friendly staff. Not the newest most updated hotel but clean.

Reviewed on Jun 6, 2024

Ossipee Essential Information

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

Ossipee Hotel Deals

Mill Falls at the Lake
Mill Falls at the Lake
3 out of 5
312 Daniel Webster Hwy, Meredith, NH
The price is $151 per night from Jun 25 to Jun 26
$151
$204 total
includes taxes & fees
Jun 25 - Jun 26
8.2/10 Very Good! (516 reviews)
"Having stayed here multiple times on the past. They have reduced the number of amenities in the rooms and past the cost of others to the guest as a resort fee. Other than these unexpected issues it's a great location with stunning views."

Reviewed on Jun 2, 2024

Mill Falls at the Lake
Fireside Inn & Suites Gilford
Fireside Inn & Suites Gilford
2.5 out of 5
17 Harris Shore Road, Gilford, NH
Fully refundableReserve now, pay when you stay
The price is $143 per night from Jul 2 to Jul 3
$143
$155 total
includes taxes & fees
Jul 2 - Jul 3
8.6/10 Excellent! (556 reviews)
"Clean easy access to the concert venue"

Reviewed on Jun 2, 2024

Fireside Inn & Suites Gilford
Green Granite Inn, Ascend Hotel Collection
Green Granite Inn, Ascend Hotel Collection
2.5 out of 5
1515 White Mountain Hwy, North Conway, NH
Fully refundableReserve now, pay when you stay
The price is $63 per night from Jun 9 to Jun 10
$63
$68 total
includes taxes & fees
Jun 9 - Jun 10
7.4/10 Good! (1,391 reviews)
"Weenjoyed our stay very much. It is the second time we have booked in to this hotel and are looking foreward to more stays in the future."

Reviewed on Jun 3, 2024

Green Granite Inn, Ascend Hotel Collection
See all 1,966 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Ossipee vacation package cost?
Perhaps less than you imagined — from as low as $425, as a matter of fact! By combining hotels, flights and car rentals into a customized vacation package, your Ossipee escape is just clicks away.
How do I get a cheap travel package to Ossipee?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we’ve got them all covered. Select the combination that best fits you and see your savings pile up. Of course, a travel package is never a one-size-fits-all. That’s why we offer more than 550 partner airlines and 1,000,000 hotel options throughout the world, which lets you customize your Ossipee getaway.
What are the top hotels in Ossipee?
Get your trip off to a good start by staying at Tentrr Signature Site - Mountain Views And Farm Animals. It’s one of most popular properties in Ossipee. Another welcoming option is Lakeside Retreat A Hidden Gem.
How far in advance should I book my Ossipee vacation?
Smart travelers often reserve their seats early. You can generally browse through international fares on Expedia up to 12 months before your flight. If you’ve left booking to the last minute, don’t stress. Bargain prices occasionally appear in the last weeks before departure dates.
What does an Expedia Ossipee travel package include?
From hotels and flights to rental cars, Expedia can help you create an Ossipee package that suits you. Heading off for a few weeks? Check out a rental car, hotel and flight bundle. If you’re taking a short break, a hotel and flight deal could be what you’re after. Activities can also be added once you’ve made your booking. Our travel packages make it a cinch to save and plan.
What should I know before booking an Ossipee travel package?
Whether it’s adventure or relaxation you’re chasing, an Ossipee vacation package lets you organize your escape your way. Plus, you’ll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with an Ossipee Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Ossipee vacation package?
If your vacation plans in Ossipee have changed, it’s comforting to know that it’s possible to cancel or amend your booking. If your booking was made in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a cancellation fee. To find out more, check our Customer Service Portal.

Other 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.