Jolly Island Vacations from $433

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Your Jolly Island Vacation

Organizing your next big getaway is a breeze with a Jolly Island vacation package. The neighborhood of South Down Shores, which is good for hiking, makes a good starting point to discover the marvels of this lively city. Make your trip to Jolly Island even more fun and exciting by including some sightseeing. Gunstock Mountain Resort, Bank of New Hampshire Pavilion at Meadowbrook and Ellacoya State Park are among the top attractions you'll want to explore. Your ideal Jolly Island vacation is just clicks away. Search flights, accommodations and more on Expedia for a trip that's tailored to suit your style.

The Latest Jolly Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Moultonborough Inn

Moultonborough Inn

3 out of 5
Price was $562, price is now $433 per person
$433
per person
Aug 1 - Aug 4
found 9 hours ago
Roundtrip flight included
Washington (WAS) to Manchester (MHT)
9/10 Wonderful! (207 reviews)
It was clean and quiet

Reviewed on May 23, 2026

The Centennial

The Centennial

4 out of 5
Price was $1,209, price is now $884 per person
$884
per person
Aug 2 - Aug 8
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
Lovely and very helpful staff - Late night and early morning! Bed was very comfortable and breakfast was out early and very nice.

Reviewed on Apr 6, 2026

The Lake Estate on Winnisquam

The Lake Estate on Winnisquam

4.5 out of 5
Save 100% on your flight
Price was $1,035, price is now $770 per person
$770
per person
Aug 1 - Aug 4
found 9 hours ago
Roundtrip flight included
Washington (WAS) to Manchester (MHT)
9.6/10 Exceptional! (18 reviews)
Resort is clean and very well designed. Service by the restaurant is not very good. Service very slow especially when there is a wedding at the venue.

Reviewed on May 18, 2026

The Inn at Thorn Hill & Spa

The Inn at Thorn Hill & Spa

4 out of 5
Save 100% on your flight
Price was $944, price is now $715 per person
$715
per person
Aug 1 - Aug 4
found 9 hours ago
Roundtrip flight included
Washington (WAS) to Manchester (MHT)
9.8/10 Exceptional! (1,004 reviews)
Lovely stay! Plan to go back

Reviewed on May 12, 2026

Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
Price was $675, price is now $528 per person
$528
per person
Aug 1 - Aug 4
found 9 hours ago
Roundtrip flight included
Washington (WAS) to Manchester (MHT)
8.8/10 Excellent! (1,002 reviews)
Love the place, stuff, property, food, beautiful room Thank you

Reviewed on May 14, 2026

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Discover the most popular places to visit in Jolly Island

Gunstock Mountain Resort

Gunstock Mountain Resort

4.5/5(64 reviews)

Hit the slopes in Gilford with a visit to Gunstock Mountain Resort. Wander the lakeside and beautiful beaches in the area.

Gunstock Mountain Resort

Bank of New Hampshire Pavilion at Meadowbrook

4.5/5(119 reviews)

You can enjoy a show at Bank of New Hampshire Pavilion at Meadowbrook during your stay in Gilford. Wander the lakeside and beautiful beaches in the area.

Bank of New Hampshire Pavilion at Meadowbrook

Ellacoya State Park

3.5/5(3 reviews)

Commune with nature and explore the great outdoors at Ellacoya State Park during your travels in Gilford. Wander the lakeside and beautiful beaches in this relaxing area.

Ellacoya State Park

Jolly Island 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
$146 nightly
The price is $159 total per night from May 25 to May 26
$159 total
May 25 - May 26
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
Steele Hill Resorts

Steele Hill Resorts

3 out of 5
516 Steele Hill Road Sanbornton NH
$189 nightly
The price is $205 total per night from May 25 to May 26
$205 total
May 25 - May 26
Total with taxes and fees
8.4/10 Very Good! (819 reviews)
"Everything was great. The restaurant was good. Loved it"

Reviewed on May 22, 2026

Steele Hill Resorts
Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $92 total per night from May 24 to May 25
$92 total
May 24 - May 25
Total with taxes and fees
6.8/10 (845 reviews)
"Great servis......................."

Reviewed on May 21, 2026

Winnisquam Lake Inn
See all 1,897 properties in Jolly Island
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 Jolly Island Vacation Packages

Jolly Island Essential Information

Language
English
Currency
U.S dollars
Top Sights
Gunstock Mountain Resort, Ellacoya State Park and Stone Gate Vineyard

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Frequently asked questions

How much does a Jolly Island vacation package cost?
You can snap up a vacation package to this popular destination from $433 on Expedia. However, how much your vacation to Jolly Island costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Jolly Island?
If you're looking to score a cheap Jolly Island vacation package, consider planning a trip in September, October and November. You'll usually find lower prices on airfares and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Jolly Island?
Generally, a handful of days is enough to tick off the top sights during your Jolly Island vacation. But if you want to have time to kick back or take day trips, think about extending your trip.
How to find the best Jolly Island package deals?
Use Expedia's filter tool to help you find some terrific Jolly Island package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Jolly Island package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Jolly Island vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Jolly Island vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Jolly Island?
If you're planning a spontaneous Jolly Island adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Jolly Island vacation packages?
Your Jolly Island break is meant to be an escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden 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.