Jolly Island Holiday Rentals

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Our top choices for Jolly Island holiday rentals

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (167)
"The apartment was great, we enjoyed the pool, jacuzzi and sauna, and the staff were super nice!!"
United States
Jenn
The price is AU$212
includes taxes & fees
11 Jan - 12 Jan 2026
Cold Spring Plymouth Resort

9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
10.0 out of 10, Exceptional, (1)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is AU$365
includes taxes & fees
16 Jan - 17 Jan 2026
9 Lake Street

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro
10.0 out of 10, Exceptional, (17)
"All excellent "
United States
Marc
The price is AU$693
includes taxes & fees
4 Jan - 5 Jan 2026
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Gorgeous Waterfront Condo with Lake Access & Views

Gorgeous Waterfront Condo with Lake Access & Views
Tilton
9.8 out of 10, Exceptional, (36)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
The price is AU$446
includes taxes & fees
5 Jan - 6 Jan 2026
Gorgeous Waterfront Condo with Lake Access & Views

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4)
"Great location & comfortable! "
United States
Jeanine L.
The price is AU$283
includes taxes & fees
2 Jan - 3 Jan 2026
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.0 out of 10, Wonderful, (2)
"We had a great time. Loved the cabin super cute. Neighborhood & neighbors very nice. The lake & private beaches were great. We enjoyed the hot tub & fire pit. I brought a few games, but you had a nice selection as well. Kitchen was very nice with everything we needed for some nice big breakfasts to start our day. We did run into a bit of a problem with the water running out. During showers, but we worked through it. Over all it was a great place. Thank you. Kim, Steve,Brianna,Cam & Brody "
United States
kim M.
The price is AU$584
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy Cottage on a Lake, near Gunstock Mountain

Modern Waterfront Condo with Views and Lake Access

Modern Waterfront Condo with Views and Lake Access
Tilton
9.4 out of 10, Exceptional, (10)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
The price is AU$517
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Waterfront Condo with Views and Lake Access

NEW Lakefront Escape Private Dock & Lake Views

NEW Lakefront Escape Private Dock & Lake Views
Alton
9.8 out of 10, Exceptional, (10)
"We stayed here because we were in town for a concert in Gilford and it was great! Perfect location, close to the venue and the lake was beautiful. It was lovely waking up to seeing the sparkling water. Would stay again. "
United States
Anna S.
The price is AU$451
includes taxes & fees
13 Jan - 14 Jan 2026
NEW Lakefront Escape Private Dock & Lake Views

Cozy Winter Escape

Cozy Winter Escape
Weirs Beach
9.2 out of 10, Wonderful, (17)
"Perfect location for Weirs beach, the boardwalk and concert venue. "
United States
Kathleen A.
The price is AU$459
includes taxes & fees
12 Jan - 13 Jan 2026
Cozy Winter Escape

Lake Access + Kayaks + Arcade + Bike Path + Deck

Lake Access + Kayaks + Arcade + Bike Path + Deck
Wolfeboro
10.0 out of 10, Exceptional, (3)
"What you see is what you get and that's a very good thing!"
United States
john a.
The price is AU$681
includes taxes & fees
2 Jan - 3 Jan 2026
Lake Access + Kayaks + Arcade + Bike Path + Deck

Retro Pines Getaway - Lake Winnipesaukee

Retro Pines Getaway - Lake Winnipesaukee
Weirs Beach
The price is AU$296
includes taxes & fees
20 Jan - 21 Jan 2026
Retro Pines Getaway - Lake Winnipesaukee

Stay in Venice our Modern Steps from the Lake with Dock!

Stay in Venice our Modern Steps from the Lake with Dock!
Alton
10.0 out of 10, Exceptional, (7)
"Very clean and in a great location."
United States
Mark B.
The price is AU$569
includes taxes & fees
30 Dec - 31 Dec
Stay in Venice our Modern Steps from the Lake with Dock!

Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (7)
"Property was very clean, had very comfortable beds and a wonderful view. "
United States
Crystal
The price is AU$249
includes taxes & fees
5 Jan - 6 Jan 2026
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.6 out of 10, Exceptional, (21)
"Great location for seeing concerts."
United States
Kevin Y.
The price is AU$376
includes taxes & fees
5 Jan - 6 Jan 2026
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Cozy condo with WiFi, fitness room in enjoyable Laconia

Cozy condo with WiFi, fitness room in enjoyable Laconia
Weirs Beach
10.0 out of 10, Exceptional, (6)
"Beautiful condo spacious and clean beautiful views loved the pool and hot tub! "
United States
Melissa D.
The price is AU$534
includes taxes & fees
12 Jan - 13 Jan 2026
Cozy condo with WiFi, fitness room in enjoyable Laconia

Inviting condo in quiet locale with partial lake views, balcony & grilling area

Inviting condo in quiet locale with partial lake views, balcony & grilling area
Gilford
8.4 out of 10, Very good, (17)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is AU$404
includes taxes & fees
4 Jan - 5 Jan 2026
Inviting condo in quiet locale with partial lake views, balcony & grilling area

Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom

Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom
Holderness
10.0 out of 10, Exceptional, (1)
"Everything was wonderful!! "
United States
Scott O.
The price is AU$609
includes taxes & fees
12 Jan - 13 Jan 2026
Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom

Lake Access, Poolside Deck & Ski Nearby

Lake Access, Poolside Deck & Ski Nearby
Gilford
8.0 out of 10, Very good, (12)
"Clean, comfortable and perfect location for our needs. Host is very responsive and easy to work with."
United States
Dan K.
The price is AU$309
includes taxes & fees
15 Jan - 16 Jan 2026
Lake Access, Poolside Deck & Ski Nearby

3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!

3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!
Laconia
9.6 out of 10, Exceptional, (8)
"The house was very spacious and newly renovated. It was. Conveniently located 15-20 minutes from the New Hampshire Motor Speedway, which was the reason for our trip. I’d love to explore more of the area on another trip. "
United States
Mary T.
The price is AU$602
includes taxes & fees
1 Jan - 2 Jan 2026
3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!

19 Mile Bay - Tuftonboro - Lake Winnipesaukee

19 Mile Bay - Tuftonboro - Lake Winnipesaukee
Tuftonboro
10.0 out of 10, Exceptional, (18)
"My stay there with my family was amazing with near by beaches and great views of the lakes. The house was very clean when we arrived and the back yard with cornhole boards was a plus over all this house and location was awesome!!"
United States
Oudom S.
19 Mile Bay - Tuftonboro - Lake Winnipesaukee
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, 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 favourite 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 depend 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 AU$212 per night. Entering your travel dates in the search wizard might find you 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 Ellacoya State Park.

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.