Jolly Island Holiday Rentals

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Our top choices for Jolly Island holiday rentals

Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is NZ$374
includes taxes & fees
14 Dec - 15 Dec
Hiking & Snowmobile Trails On-site: Alton Retreat!

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 NZ$769
includes taxes & fees
16 Dec - 17 Dec
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 NZ$511
includes taxes & fees
16 Dec - 17 Dec
Gorgeous Waterfront Condo with Lake Access & Views

Quaint house in tranquil Wolfeboro perfect for getaway

Quaint house in tranquil Wolfeboro perfect for getaway
2.0 star property
Wolfeboro
The price is NZ$534
includes taxes & fees
27 Dec - 28 Dec
Quaint house in tranquil Wolfeboro perfect for getaway

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (161)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
The price is NZ$247
includes taxes & fees
8 Jan - 9 Jan 2026
Cold Spring Plymouth Resort

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4)
"We had a perfect stay. Super cute cabin, clean and very comfortable.We thoroughly enjoyed or time there. Very easy process and would absolutely recommend and book again."
United States
Jessica G.
The price is NZ$318
includes taxes & fees
15 Dec - 16 Dec
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cute Cedar Lodge Studio with Balcony & Lake Views!

Cute Cedar Lodge Studio with Balcony & Lake Views!
Weirs Beach
9.6 out of 10, Exceptional, (15)
"Enjoyed our stay. "
United States
Ilene T.
The price is NZ$289
includes taxes & fees
5 Jan - 6 Jan 2026
Cute Cedar Lodge Studio with Balcony & Lake Views!

2BR Condo with Private Patio

2BR Condo with Private Patio
Weirs Beach
10.0 out of 10, Exceptional, (1)
"The property managers were very easy to get a hold of and responded to our request quickly."
United States
Kimberly
The price is NZ$346
includes taxes & fees
14 Dec - 15 Dec
2BR Condo with Private Patio

Warm and Cozy Condo: Perfect for Fall Foliage Getaways!

Warm and Cozy Condo: Perfect for Fall Foliage Getaways!
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 NZ$525
includes taxes & fees
14 Dec - 15 Dec
Warm and Cozy Condo: Perfect for Fall Foliage Getaways!

Mountainside chalet with a sauna and beautiful views near Lake Winnipesaukee NH!

Mountainside chalet with a sauna and beautiful views near Lake Winnipesaukee NH!
New Durham
10.0 out of 10, Exceptional, (1)
"Suxhh a beautiful and well kept home. Relaxing there was our favorite part of the trip!"
United States
Justin G.
The price is NZ$749
includes taxes & fees
19 Dec - 20 Dec
Mountainside chalet with a sauna and beautiful views near Lake Winnipesaukee NH!

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 NZ$443
includes taxes & fees
14 Dec - 15 Dec
Inviting condo in quiet locale with partial lake views, balcony & grilling area

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 NZ$490
includes taxes & fees
22 Dec - 23 Dec
Cozy condo with WiFi, fitness room in enjoyable Laconia

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 NZ$682
includes taxes & fees
22 Dec - 23 Dec
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, (9)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
The price is NZ$593
includes taxes & fees
16 Dec - 17 Dec
Modern Waterfront Condo with Views and Lake Access

The Lake View Nook - Lake Winnipesaukee

The Lake View Nook - Lake Winnipesaukee
Weirs Beach
The price is NZ$322
includes taxes & fees
6 Jan - 7 Jan 2026
The Lake View Nook - Lake Winnipesaukee

Taigh Loch - Lakes Region Retreat!

Taigh Loch - Lakes Region Retreat!
Alton
9.8 out of 10, Exceptional, (13)
"Great place! Owners were very responsive with any questions we had. Per friendly was a plus. We would definitely stay here again."
United States
Shawn M.
The price is NZ$585
includes taxes & fees
15 Dec - 16 Dec
Taigh Loch - Lakes Region Retreat!

Lake view condo, Private Beach, Private concert entrance, pool

Lake view condo, Private Beach, Private concert entrance, pool
Gilford
9.6 out of 10, Exceptional, (21)
"Great location for seeing concerts."
United States
Kevin Y.
The price is NZ$429
includes taxes & fees
23 Dec - 24 Dec
Lake view condo, Private Beach, Private concert entrance, pool

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 NZ$630
includes taxes & fees
17 Dec - 18 Dec
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

Private Dock, Boat Access & Sunrise Views

Private Dock, Boat Access & Sunrise Views
Meredith
The price is NZ$1,068
includes taxes & fees
15 Dec - 16 Dec
Private Dock, Boat Access & Sunrise Views

Siena/Venice waterfront private units (2) with 2 Docks!

Siena/Venice waterfront private units (2) with 2 Docks!
Alton
The price is NZ$869
includes taxes & fees
14 Dec - 15 Dec
Siena/Venice waterfront private units (2) with 2 Docks!
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 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 NZ$247 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 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.