Holiday Rentals in Jolly Island

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Our top choices for Jolly Island holiday rentals

Cold Spring Plymouth Resort

3.5 star property
Ashland
9.2 out of 10, Wonderful, (159)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
The price is €123
includes taxes & fees
8 Jan - 9 Jan 2026
Cold Spring Plymouth Resort

Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

Alton
10.0 out of 10, Exceptional, (15)
"We thoroughly enjoyed our stay at your cozy, clean, comfy cabin. It was a fun place to spend our couple of days of vacation "
United States
Jackie r.
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Alton
8.6 out of 10, Excellent, (18)
"Location was A, however the overall place is very dated. One small pan to cook, along with a lobster pot. Furniture and bedding needs updating, along with interior. It is a great setting with lots of potential."
United States
Hubert B.
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Gilford
9.8 out of 10, Exceptional, (179)
"The house was amazing! The pool and sauna area felt like a resort. I am looking for an excuse to go back. "
United States
Maggie B.
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Baby Chocorua A Frame in the mountains sleeps 8

Chocorua
10.0 out of 10, Exceptional, (18)
"Beautiful house with great amenities. "
United States
Bill P.
The price is €466
includes taxes & fees
15 Dec - 16 Dec
Baby Chocorua A Frame in the mountains sleeps 8

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Alton
9.4 out of 10, Exceptional, (25)
"Perfect waterfront stay but did not like being so close to the road."
United States
Lucas T.
The price is €308
includes taxes & fees
24 Dec - 25 Dec
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Close to downtown Meredith & lake Winnipesaukee on 13 secluded acres, Mt. views

Meredith
10.0 out of 10, Exceptional, (234)
"Very clean cabin good for relaxation and beautiful sunsets"
United States
Darla J.
Close to downtown Meredith & lake Winnipesaukee on 13 secluded acres, Mt. views

Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

Moultonborough
10.0 out of 10, Exceptional, (58)
"Had an excellent stay, would highly recommend!"
United States
Chris V.
Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

New Lakefront Home sleeps 14 with dock.

Alton
8.6 out of 10, Excellent, (67)
"Convenient location, Host was great and responsive. Good place to be at with a few friends "
United States
Collin G.
The price is €828
includes taxes & fees
26 Dec - 27 Dec
New Lakefront Home sleeps 14 with dock.

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Weirs Beach
10.0 out of 10, Exceptional, (15)
"Everything was great…and the hosts quickly responded to any requests for help with anything."
United States
William M.
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

Gilford
7.8 out of 10, Good, (45)
"The home was perfect for our stay! "
United States
Amy S.
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

Charming Bungalo Village Cottage on Newfound Lake

Bristol
9.4 out of 10, Exceptional, (95)
"It was a getaway and to visit friends "
United States
Kristin B.
Charming Bungalo Village Cottage on Newfound Lake

New Home Private Pool/Hot Tub Near Meredith Center

Meredith
9.6 out of 10, Exceptional, (51)
"We enjoyed staying in this beautiful home."
United States
D M.
New Home Private Pool/Hot Tub Near Meredith Center

Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

Gilford
9.4 out of 10, Exceptional, (143)
"This was a great getaway spot for my husband and I to take a quick weekend trip! We came up for a concert, which was great as we were so close we walked over! Owner was wonderful and very responsive. We will definitely re book for the next lake trip or concert! "
United States
Sarah M.
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

Alton
9.6 out of 10, Exceptional, (14)
"Very neat place"
United States
Scott
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

New Charming Chalet with Lake Winni Views

Alton
9.4 out of 10, Exceptional, (3)
"Great house with a great location. Super responsive and having a slip to use makes the location perfect. "
United States
Ryan D.
New Charming Chalet with Lake Winni Views

Cabin with lake views & lake access Now featuring AC Wi-FI and TV sleeps 5

Alton
9.4 out of 10, Exceptional, (9)
"Great place to stay! Tons of games and fire pits all around. I wish we had stayed longer to enjoy it all."
United States
Tara L.
Cabin with lake views & lake access Now featuring AC Wi-FI and TV sleeps 5

Waterfront home with wraparound deck, floating fireplace, deck, & firepit

Center Barnstead
7.0 out of 10, Good, (33)
"Loved our stay."
United States
Judy C.
Waterfront home with wraparound deck, floating fireplace, deck, & firepit

Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

Gilford
9.8 out of 10, Exceptional, (16)
"We really enjoyed our stay at this property. It was very clean and well stocked and a nice location to get to activities around the lake.The host was very pleasant and easy to communicate with. We hope to stay again in the future."
United States
Linda N.
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Sanbornton
10.0 out of 10, Exceptional, (13)
"Great location, great kitchen, great bedding"
United States
Wanaka G.
The price is €612
includes taxes & fees
12 Dec - 13 Dec
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
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.
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Top Jolly Island Hotel Reviews

Find out more about Jolly Island

Everything you need to know about Jolly Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jolly Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jolly Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jolly Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jolly Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jolly Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jolly Island holiday rentals we have selected for you start as low as €123 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jolly Island rentals

At Expedia, we put the best Jolly Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jolly Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jolly Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jolly Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Jolly Island?

Yes, there are holiday rentals close to the most popular sights in Jolly Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Jolly Island has to offer?

Cold Spring Plymouth Resort: This holiday home rental outside of Jolly Island is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. You can relax into your holiday with an outdoor tennis court and 1 hot tub.

What can I see and do in Jolly Island?

Explore the area and family-friendly sights such as Funspot Family Fun Center, or get out into nature at a spot like Lake Winnipesaukee. In the wider area, you’ll find Bank of New Hampshire Pavilion at Meadowbrook and Weirs Beach.

What are holiday rentals like in Jolly Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jolly Island. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.