Jolly Island Holiday Rentals

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Holiday Rentals in Jolly Island

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

10.0 out of 10, Exceptional, (157)
"The location is exceptional. The pool area, steam room, sauna, and total recreation area were amazing. The pool temperature (air and water) was good for this time of year. The consistent 4 foot pool depth made it great for a community water volley ball game. (*We are all over 65) Having 5 "king bedrooms with three bathrooms in three different areas of the house allowed the entire adult group comfort and privacy. We also made use of the 2 bathrooms near the pool. The extra large living...
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Deck For Entertaining: Belmont Group Getaway

9.0 out of 10, Wonderful, (65)
"This house was such a find. It sleeps so many adults comfortably. There is so much space and comfortable couches. The kitchen is well stocked with pans and platters, etc. Check in and check out were really easy. It was the best house we could have asked for."
Deck For Entertaining: Belmont Group Getaway

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

8.8 out of 10, Excellent, (19)
"Great time."
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

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!🏔☀️🏊‍♀️⛷

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (23)
"Beautiful home. Great weekend away!! "
Cozy, Pet-Friendly Escape Near Lake & Mountains

Cold Spring Resort

3.5 star property
9.0 out of 10, Wonderful, (98)
"2 level condo is nice. A little tricky to find in the dark. Arrive in the daylight or get additional details than what’s on the “map” at check in."
Cold Spring Resort

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

6.4 out of 10, (19)
"The house was nice but needs updates. The view was absolutely gorgeous and very easy to get too."
Waterfront home with wraparound deck, floating fireplace, deck, & firepit

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

8.8 out of 10, Excellent, (15)
"We stay. In Alton Bay each year for a couple of concerts at Bank of NH Pavilion in Gilford. We extend it by staying for a couple of days at Lake Winnipesaukee The motel is perfectly located close to the venue and on the lake for swimming and boating while visiting BNH Pavilion. The motel is in a pine grove and is lake front. It's "!old school " feel reminds of my childhood. It's clean and quite, but no thrills. Don't expect first class accommodations but if you like the feel of a...
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

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

8.6 out of 10, Excellent, (24)
"Nice home, close to bank of NH pavilion, and Weirs beach. "
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

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

10.0 out of 10, Exceptional, (7)
"Great location, beautiful house , we were a bit upset that the outside hot tub was not available even though it was listed as part of the amenities."
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

6.8 out of 10, (9)
"I didn’t look close at the on-line pics so at first arrival I had concerns. It’s a charming older style lake house that could use a bit of pampering but it was very clean and comfortable for our group of 8. The host and management company were great and easy to communicate with. We came up for our daughter’s wedding and we all had a very nice weekend. Thank you"
Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

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

Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome

10.0 out of 10, Exceptional, (160)
"Wouldn’t change a thing! The house was wonderful and Sharon was amazing. Had a great vacation and would definitely stay here again."
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome

New Hampshire Getaway w/ Game Room & Lake Access

9.6 out of 10, Exceptional, (4)
"Great layout- loved the porch/deck at night Game room is an amazing addition Everyone loved it!"
New Hampshire Getaway w/ Game Room & Lake Access

Newly Renovated Rustic Cabin

9.6 out of 10, Exceptional, (253)
"Nice cozy cabin very beautiful inside"
Newly Renovated Rustic Cabin

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

10.0 out of 10, Exceptional, (86)
"Hanna was a wonderful host! When we had an issue with water pressure in the shower, she responded within minutes and had someone out to fix it within about an hour. The place is rustic but charming with a great fireplace!"
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

Waterfront Ashland Home ~ 2 Mi to Downtown!

8.4 out of 10, Very good, (7)
"We stayed for a short family vacation. The house was just as pictured. Everything we needed was supplied. The kids loved swimming and fishing right were we stayed!"
Waterfront Ashland Home ~ 2 Mi to Downtown!

Winnipesaukee Lakefront Home with Dock & Views!

9.4 out of 10, Exceptional, (61)
"Interior of the home was very nice. Access to water was difficult and made worse by the lack of pruning of the bushes that had grown into the already narrow stairway leading to the dock. Parking was difficult, additional information regarding possible places to park another vehicle or trailer would be helpful. A broom and functioning vaccum would also have been helpful. Dock boards, posts, and cletes, were loose in multiple locations with exposed nails facing upwards. Multiple dirty dishes in...
Winnipesaukee Lakefront Home with Dock & Views!

Cozy Cottage on Lake Winni

9.2 out of 10, Wonderful, (33)
"This cabin was close to most attractions in the area. The cabin was clean and was perfect for our stay!"
Cozy Cottage on Lake Winni

Family Friendly Rustic Newly Renovated Cabin Abutting The White Lake State Park.

9.6 out of 10, Exceptional, (243)
"Make sure you bring your own towels"
Family Friendly Rustic Newly Renovated Cabin Abutting The White Lake State Park.
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

Best Western Plymouth Inn-White Mountains

2.5 star property
9.0 out of 10, Wonderful, (685)
"Very comfortable, very clean, great included breakfast!"
The price is NZ$186
includes taxes & fees
1 Dec - 2 Dec
Best Western Plymouth Inn-White Mountains

Steele Hill Resorts

3.0 star property
8.4 out of 10, Very good, (573)
"Beautiful place"
The price is NZ$296
includes taxes & fees
1 Dec - 2 Dec
Steele Hill Resorts

Best Western Plus Landmark Inn

2.5 star property
7.6 out of 10, Good, (956)
"Extremely clean, courteous staff."
The price is NZ$190
includes taxes & fees
1 Dec - 2 Dec
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Jolly Island is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.