Jolly Island Vacations from $332

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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.
Sunset Hill House

Sunset Hill House

4 out of 5
Price was $444, price is now $332 per person
$332
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
8.8/10 Excellent! (1,000 reviews)
Very friendly staff and has a beautiful viewpoint

Reviewed on Dec 28, 2025

Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Save 100% on your flight
Price was $700, price is now $471 per person
$471
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Lebanon (LEB)
9.6/10 Exceptional! (886 reviews)
I truly enjoyed my time. The Hanover Inn is charming, clean, and festively decorated. It is located in a prime location with walking distance to everything I needed. The staff is helpful and friendly. Valet parking was convenient in the cold winter. I would definitely stay here again. I stayed when Dartmouth was on winter break. The campus is outstanding and inspiring.

Reviewed on Jan 1, 2026

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
Save 100% on your flight
Price was $569, price is now $422 per person
$422
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Miami (MIA) to Manchester (MHT)
9.4/10 Exceptional! (38 reviews)
Innkeeper Josh deserves every single star in this review.

Reviewed on Jan 7, 2026

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
Price was $818, price is now $627 per person
$627
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
7/10 Good! (1,000 reviews)
The overall stay was excellent check in to check out

Reviewed on Jan 9, 2026

Cranmore Mountain Lodge Bed & Breakfast

Cranmore Mountain Lodge Bed & Breakfast

3 out of 5
Kearsarge
Price was $956, price is now $734 per person
$734
per person
Feb 14 - Feb 18
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Manchester (MHT)
8.8/10 Excellent! (244 reviews)
everything was great

Reviewed on Jan 1, 2026

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Discover the most popular places to visit in Jolly Island

The View Panoroma of 4 pictures taken from the top of Gunstock mountain.

Gunstock Mountain Resort

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

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

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

Winnisquam Lake Inn

Winnisquam Lake Inn

3 out of 5
788 Laconia Rd Tilton NH
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Jan 11 to Jan 12
$97 total
Jan 11 - Jan 12
Total with taxes and fees
6.6/10 (820 reviews)
Excellent

Reviewed on Dec 4, 2025

Winnisquam Lake Inn
The Common Man Inn & Spa

The Common Man Inn & Spa

4 out of 5
231 Main St Plymouth NH
9/10 Wonderful! (391 reviews)
No complaints, great setting and staff was polite and welcoming

Reviewed on Jan 5, 2026

Get rates
The Common Man Inn & Spa
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

3 out of 5
281 Daniel Webster Hwy Meredith NH
$149 nightly
The price is $162 total per night from Feb 1 to Feb 2
$162 total
Feb 1 - Feb 2
Total with taxes and fees
8.2/10 Very Good! (916 reviews)
We come here specifically for the hot tubs and indoor outdoor pool. Such an amazing experience! Restaurant in Church landing was great. Short rib prepared perfectly! Only bad part is that you have to walk outside to get to the pool/hot tub if you rooms aren't adjacent to that area. Not a big deal ...

Reviewed on Jan 5, 2026

Mill Falls Resort Collection at the Lake
See all 1,747 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 $332 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.