Jolly Island Holiday Rentals

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Holiday Rentals in Jolly Island

Cold Spring Plymouth Resort

3.5 star property
9.0 out of 10, Wonderful, (112)
"Great stay for family, spacious, plenty room for sleep and just hang out. The only issue was that one of the rooms heater barely worked, but it was just 2 of us this time, so wasn't a big issue. Definitely will come. "
The price is NZ$219
includes taxes & fees
16 Apr - 17 Apr
Cold Spring Plymouth Resort

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

10.0 out of 10, Exceptional, (167)
"Massive 7,000 sq ft. super cool house close to Gunstock that felt like we rented an entire commercial lodge. Bedrooms and baths for everyone, large indoor pool, hot tub, steam and sauna, bar area, game room, and huge fireplaced dining room with seating for 20! Kids were ecstatic and we had the best time. Clean, responsive and pleasant owner as well. If you have a large family, this is the place...you won't be disappointed!PatrickMarshfield, MA"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.8 out of 10, Exceptional, (21)
"As a family of 6, our options are limited to 2 hotel rooms or a vacation property. This property exceeded all expectations. Perfect balance between feeling like a family vacation home and an elevated rental property without being full luxury with the typical higher price tag. Will definitely return. "
The price is NZ$857
includes taxes & fees
28 Apr - 29 Apr
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

8.8 out of 10, Excellent, (19)
"It’s no wonder that the house resides on Paradise Drive. An absolute slice of heaven. This was our second time staying here and we can’t wait to book again. You can’t beat the location when you are a short walk to the lively public beach while also sitting on a cool quiet tributary with a private dock. The home is clean and comfortable with multiple wall mounted AC units to escape the summer heat. Two bedrooms with plenty of space for air mattresses makes this place great for families or...
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

New Lakefront Home sleeps 14 with dock.

8.8 out of 10, Excellent, (61)
"Location is very convenient - grocery within a 10 min ride, easy access to the Lake, dining, and popular Winnipesaukee villages around the lake. The amenities were generous - including towels and linens at the location, travel shampoo/condition/soaps available, fully stocked kitchen with dish soap and other kitchen tools available. The kitchen is tight and the central artery of the house, which made it difficult with 12 people. I'd recommend bringing a mattress pad or something for the pull...
New Lakefront Home sleeps 14 with dock.

Lake Access, Mtn Views, Game Room, Hot Tub & More!

Lake Access, Mtn Views, Game Room, Hot Tub & More!

My Mountainside Mansion in Waterville Estates!🏔☀️🏊‍♀️⛷

9.8 out of 10, Exceptional, (9)
"Had a fun weekend with friends and Family. The house had everything that we need. The views are amazing. Thank you Joshua for hosting us. "
My Mountainside Mansion in Waterville Estates!🏔☀️🏊‍♀️⛷

Lakefront Alton Bay Retreat w/ Dock Near Beaches!

9.6 out of 10, Exceptional, (5)
"Great location for us. We are going to a Camp Kabeyun reunion and it was very convenient. There was some cleanliness issues with crumbs and such but overall the property was great."
Lakefront Alton Bay Retreat w/ Dock Near Beaches!

The Gnome Home Cottage located near white mountain NH

9.6 out of 10, Exceptional, (46)
"Lovely little Aframe with lots of charm! James was great host, very easy to work with and attentive. The gnome decor adorable the kids loved it! Really nice space overall. We look forward to our next visit."
The price is NZ$523
includes taxes & fees
5 Apr - 6 Apr
The Gnome Home Cottage located near white mountain NH

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (30)
"Charming, clean and lovely place to stay. Owners were very easy to communicate with. Place was gorgeous. We had a great time. We would definitely stay here again and highly recommend it!!! "
The price is NZ$738
includes taxes & fees
27 Apr - 28 Apr
Cozy, Pet-Friendly Escape Near Lake & Mountains

Lake Winnipesaukee Retreat with Beach & Boat Dock Access! Dog Friendly!

Lake Winnipesaukee Retreat with Beach & Boat Dock Access! Dog Friendly!

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (17)
"The place was quaint, modern and lovely. The views were fabulous! "
The price is NZ$664
includes taxes & fees
9 Apr - 10 Apr
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

9.0 out of 10, Wonderful, (8)
"The house was clean and comfortable. It was roomy. The views were great. The owners were helpful and friendly. We would stay here again. "
4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

The view-Enjoy Lake Winni both on & off the water-outdoor enthusiasts dream

2.5 star property
10.0 out of 10, Exceptional, (1)
"Amazing location and views on the lake. The property was super clean with everything we needed for a comfortable stay. We were in Gilford for a ski trip and we the house was located just 19 min away from the slopes! Great communication with the management that was very pro active giving checkin and checkout info. 100% recommend! "
The view-Enjoy Lake Winni both on & off the water-outdoor enthusiasts dream

Secluded Waterfront Real Estate - Dams Beach

9.0 out of 10, Wonderful, (36)
"We stayed there for Laconia weekend 2024. 4 couples were very comfortable. The street up to a certain part to get to location is paved then dirt. The driveway dirt and rocks which is rough especially for motorcycle. Owner allowed easy early check in and we were able to park motorcycles in garage which was awesome. Home could use some maintenance but overall nice. The location was quiet and secluded. Only downfall with the location for us is distance not walkable to get to weirs strip which we...
Secluded Waterfront Real Estate - Dams Beach

Lake Winnipesaukee Escape: Beach & Dock Access! Dog Friendly! Game Room!

Lake Winnipesaukee Escape: Beach & Dock Access! Dog Friendly! Game Room!

Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

9.8 out of 10, Exceptional, (96)
"I met up with a friend who lives 3 states away now...So we decided to have a weekend get-together - this was the perfect place! Clean and comfortable. The couch and chairs were very comfortable, beds were very comfortable, the kitchen was well-supplied. We had a great time, and the hosts were very accessible. There had been a strong wind storm that had affected the utilities, but the hosts stayed informed and in touch with us, and everything was taken care of in a timely manner. I would...
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

Charming dog-friendly lakefront cottage with private dock & community beach

8.8 out of 10, Excellent, (5)
"Great spot, great doc, great everything. It was a little small. but still nice. The only thing that it lacked was a couple of AC units because it gets very hot if it is a hot humid day especially upstairs in the loft."
Charming dog-friendly lakefront cottage with private dock & community beach

Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

9.6 out of 10, Exceptional, (133)
"We really enjoyed our stay. The condo was comfortable, clean, had everything you needed and was in a great location. We enjoyed walking across the street to the lake and up the hill to go the concert next door. We were also a short drive from Weirs Beach. We had great communication and hope to stay there again."
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

Beautiful private rustic log cabin, pool, hot tub

10.0 out of 10, Exceptional, (49)
"We found the cabin to be fairly comfortable. The double bed in the basement was uncomfortable for two people. Some tilting of the mattress due to poor construction. The cabin could use more lighting (some strategically placed lamps.) It seemed dark in the evening. Although there is a nice fireplace, please be aware that you have to bring your own wood. Also, if you want to use the grill, you have to bring the propane tank somewhere to get it filled."
Beautiful private rustic log cabin, pool, hot tub
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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Other types of properties in Jolly Island you may be interested in

Mill Falls Resort Collection at the Lake

3.0 star property
8.2 out of 10, Very good, (671)
"The stay was relaxing and comfortable. Its a great location with great views and lots of places with good food. The room was nice, not super highend but for the most part clean and cozy with a functional glass incased gas powered fireplace. The only thing that was a little inconvenient was because this resort has multiple buildings that are not close by on the same plot of land. Each building is a ride back out to the main road and a light or two either on the left or right. With that said, the...
The price is NZ$271
includes taxes & fees
14 Apr - 15 Apr
Mill Falls Resort Collection at the Lake

Best Western Plymouth Inn-White Mountains

2.5 star property
9.0 out of 10, Wonderful, (753)
"Very friendly staff"
The price is NZ$162
includes taxes & fees
7 Apr - 8 Apr
Best Western Plymouth Inn-White Mountains

Best Western Plus Landmark Inn

2.5 star property
7.6 out of 10, Good, (1001)
"Great"
The price is NZ$193
includes taxes & fees
6 Apr - 7 Apr
Best Western Plus Landmark Inn
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.

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.