Holiday Rentals in Jolly Island

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Our top choices for Jolly Island holiday rentals

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (11 reviews)
"Great property. Loved our stay and the owners were great! Definitely will book again "
United States
Marcus
The price is €160
includes taxes & fees
11 Mar - 12 Mar
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"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 €162
includes taxes & fees
11 Mar - 12 Mar
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

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 reviews)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is €229
includes taxes & fees
11 Mar - 12 Mar
Inviting condo in quiet locale with partial lake views, balcony & grilling area

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Gilmanton
9.6 out of 10, Exceptional, (34 reviews)
"Nice quiet visit. Lovely to be so close to the lake!"
United States
Phyllis S.
The price is €293
includes taxes & fees
11 Mar - 12 Mar
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

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, (18 reviews)
"Booked a summer getaway for my husband, my dog, and me. We had a great time - the house was comfortable and clean, and the location was excellent! "
United States
Laura B.
The price is €457
includes taxes & fees
11 Mar - 12 Mar
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Modern Waterfront Condo with Views and Lake Access

Modern Waterfront Condo with Views and Lake Access
Tilton
9.6 out of 10, Exceptional, (11 reviews)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
The price is €291
includes taxes & fees
11 Mar - 12 Mar
Modern Waterfront Condo with Views and Lake Access

2 Bdrm Condo walking distance to Weirs Beach and much more!!

2 Bdrm Condo walking distance to Weirs Beach and much more!!
Weirs Beach
9.6 out of 10, Exceptional, (55 reviews)
"Great location, easy and smooth stay!"
United States
Aimee M.
The price is €236
includes taxes & fees
14 Mar - 15 Mar
2 Bdrm Condo walking distance to Weirs Beach and much more!!

Gorgeous Waterfront Condo with Lake Access & Views

Gorgeous Waterfront Condo with Lake Access & Views
Tilton
9.8 out of 10, Exceptional, (38 reviews)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
The price is €260
includes taxes & fees
17 Mar - 18 Mar
Gorgeous Waterfront Condo with Lake Access & Views

Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is €218
includes taxes & fees
15 Mar - 16 Mar
Hiking & Snowmobile Trails On-site: Alton Retreat!

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, (23 reviews)
"Clean,well kept,very nice decorNice location"
United States
Jeannette H.
The price is €181
includes taxes & fees
17 Mar - 18 Mar
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Alton
9.4 out of 10, Exceptional, (25 reviews)
"Great location, easy access and very clean. The only negative was the paper-thin walls or should I say neighbors that did not think of anyone else or their neighbors."
United States
Lisa D.
The price is €322
includes taxes & fees
24 Mar - 25 Mar
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

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 reviews)
"Property was very clean, had very comfortable beds and a wonderful view. "
United States
Crystal
The price is €166
includes taxes & fees
18 Mar - 19 Mar
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is €189
includes taxes & fees
6 Apr - 7 Apr
Stunning Lake Views close to Weirs Beach & Gunstock

Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Wolfeboro
8.0 out of 10, Very good, (17 reviews)
"Thanks for a great stay!"
United States
Lynne Q.
The price is €298
includes taxes & fees
11 Mar - 12 Mar
Cozy three bedroom house located just five minutes from Lake Winnipesaukee

large-group mountain/lake getaway

large-group mountain/lake getaway
Gilford
9.6 out of 10, Exceptional, (18 reviews)
"We were very pleased with accommodations. We are 4 adults and the house had everything we needed for our visit. The beds were comfortable and the house was very clean. All communication with the host was answered quickly."
United States
Ruth R.
The price is €547
includes taxes & fees
22 Mar - 23 Mar
large-group mountain/lake getaway

Lake Access + Kayaks + Arcade + Bike Path + Deck

Lake Access + Kayaks + Arcade + Bike Path + Deck
Wolfeboro
10.0 out of 10, Exceptional, (3 reviews)
"What you see is what you get and that's a very good thing!"
United States
john a.
The price is €274
includes taxes & fees
11 Mar - 12 Mar
Lake Access + Kayaks + Arcade + Bike Path + Deck

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (195 reviews)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
The price is €124
includes taxes & fees
24 Mar - 25 Mar
Cold Spring Plymouth Resort

[NEW] Cozy Cabin near Gunstock & Lake Winni

[NEW] Cozy Cabin near Gunstock & Lake Winni
Gilford
10.0 out of 10, Exceptional, (1 review)
"Great spot, especially for skiing at Gunstock. Very clean and comfortable. Host was available and responsive. Will definitely be coming back!"
United States
David H.
The price is €512
includes taxes & fees
17 Mar - 18 Mar
[NEW] Cozy Cabin near Gunstock & Lake Winni

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.4 out of 10, Exceptional, (3 reviews)
"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 €338
includes taxes & fees
12 Mar - 13 Mar
Cozy Cottage on a Lake, near Gunstock Mountain

Cozy 1-Bedroom Cottage Meredith shared beach with AC

Cozy 1-Bedroom Cottage Meredith shared beach with AC
Meredith
The price is €363
includes taxes & fees
11 Mar - 12 Mar
Cozy 1-Bedroom Cottage Meredith shared beach with AC
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 €124 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, an outdoor tennis court and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind.

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.