Jolly Island Vacations from $301

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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.
The Centennial

The Centennial

4 out of 5
Price was $470, price is now $301 per person
$301
per person
Feb 5 - Feb 8
found 10 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Manchester (MHT)
17.6/10 Exceptional! (1,000 reviews)
The staff were great. The room was clean and nice. We had a window problem that was corrected quickly. Toiletries were fine. The only reason for a 4 rating is the continental breakfast was not good - the bagels, muffins & pastry were stale and the coffee was not good. It was a great location. Unfortunately many stores and restaurants were closed on Sundays & Mondays, not the hotel’s fault something to note if visiting Concord NH.

Reviewed on Nov 18, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Price was $791, price is now $548 per person
$548
per person
Jan 5 - Jan 8
found 5 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Manchester (MHT)
19.2/10 Exceptional! (352 reviews)
Loved our stay was very relaxing, had room with fireplace, it was wonderful! Love the dining options! Great for a quick weekend trip!

Reviewed on Nov 16, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $803, price is now $606 per person
$606
per person
Feb 5 - Feb 9
found 16 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Lebanon (LEB)
18/10 Exceptional! (774 reviews)
Very welcoming, spacious, clean. Perfect for a family of 4.

Reviewed on Nov 18, 2025

Hampton Inn & Suites Manchester-Bedford

Hampton Inn & Suites Manchester-Bedford

2.5 out of 5
Price was $418, price is now $331 per person
$331
per person
Feb 5 - Feb 8
found 10 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Manchester (MHT)
16.8/10 Exceptional! (1,006 reviews)
Room was good size and spotless. Staff was outstanding. Everyone was very helpful and attentive.

Reviewed on Nov 22, 2025

Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

2.5 out of 5
Price was $386, price is now $311 per person
$311
per person
Feb 5 - Feb 8
found 10 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Manchester (MHT)
17.2/10 Exceptional! (1,002 reviews)
Courteous staff, clean room, and a mice breakfast. All I wanted.

Reviewed on Nov 9, 2025

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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
$77 nightly
The price is $83 total per night from Nov 24 to Nov 25
$83 total
Nov 24 - Nov 25
Total with taxes and fees
6.6/10 (806 reviews)
The room was nice but a little small and drafty. The family was really cool though, once you got got to know them. For the price you really couldnt complain. It averaged about 90$ a night, waffles, cereal, fruit and yogurts for breakfast, coffee, ice and microwave by the office. Really nice on the ...

Reviewed on Nov 19, 2025

Winnisquam Lake Inn
The Common Man Inn & Spa

The Common Man Inn & Spa

4 out of 5
231 Main St Plymouth NH
$103 nightly
The price is $112 total per night from Nov 25 to Nov 26
$112 total
Nov 25 - Nov 26
Total with taxes and fees
9/10 Wonderful! (386 reviews)
Just one night but the beds were comfortable and the room was immaculate. Would definitely recommend for the Plymouth area.

Reviewed on Nov 10, 2025

The Common Man Inn & Spa
TownePlace Suites by Marriott Gilford

TownePlace Suites by Marriott Gilford

3 out of 5
14 Sawmill Road Gilford NH
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $145 total per night from Dec 8 to Dec 9
$145 total
Dec 8 - Dec 9
Total with taxes and fees
9.2/10 Wonderful! (622 reviews)
Great location, warm, friendly staff.

Reviewed on Nov 8, 2025

TownePlace Suites by Marriott Gilford
See all 1,740 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 $301 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.