Jolly Island Hotels with Swimming Pool

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Check availability on Jolly Island Hotels with Swimming Pools

Our top choices for Jolly Island hotels with a pool

Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
The Windrifter Resort

The Windrifter Resort

The Windrifter Resort
2.5 star property
Wolfeboro
8.8 out of 10, Excellent, (364)
"Room was clean and comfortable close to the area we needed to visit"
United States
Thomas
The price is RM460
RM500 total
includes taxes & fees
17 Dec - 18 Dec
The Windrifter Resort
Seasonal outdoor pool
Lake Wentworth Inn

Lake Wentworth Inn

Lake Wentworth Inn
2.0 star property
Wolfeboro
9.4 out of 10, Exceptional, (516)
"Clean and the staff was very helpful and kind."
United States
Justin
The price is RM512
RM556 total
includes taxes & fees
17 Dec - 18 Dec
Lake Wentworth Inn
Outdoor pool
Mount Whittier Motel

Mount Whittier Motel

Mount Whittier Motel
2.5 star property
Center Ossipee
7.8 out of 10, Good, (258)
"Clean rooms, staff was accommodating "
United States
Kenneth
The price is RM287
RM321 total
includes taxes & fees
30 Dec - 31 Dec
Mount Whittier Motel
Indoor pool
Days Inn by Wyndham Tamworth

Days Inn by Wyndham Tamworth

Days Inn by Wyndham Tamworth
2.5 star property
Chocorua
7.2 out of 10, Good, (575)
The price is RM364
RM395 total
includes taxes & fees
18 Dec - 19 Dec
Days Inn by Wyndham Tamworth
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers
Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford
2.5 star property
Gilford
8.8 out of 10, Excellent, (920)
"The staff was very nice and efficient, the room was clean and comfortable. "
United States
Janet
The price is RM550
RM597 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fireside Inn & Suites Gilford
Indoor pool, outdoor pool, pool loungers
Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake
3.0 star property
Meredith
8.4 out of 10, Very good, (912)
"Great staff clean room"
United States
Nicole
The price is RM352
RM558 total
includes taxes & fees
14 Jan - 15 Jan 2026
Mill Falls Resort Collection at the Lake
Indoor pool
TownePlace Suites by Marriott Gilford

TownePlace Suites by Marriott Gilford

TownePlace Suites by Marriott Gilford
3.0 star property
Gilford
9.2 out of 10, Wonderful, (629)
"Great location, warm, friendly staff."
United States
Charles
The price is RM585
RM635 total
includes taxes & fees
23 Dec - 24 Dec
TownePlace Suites by Marriott Gilford
Indoor pool
Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

Best Western Plus Landmark Inn
2.5 star property
Laconia
7.8 out of 10, Good, (1002)
"Nice place very clean rooms breakfast nice front desk nice people "
United States
Luis
The price is RM431
RM468 total
includes taxes & fees
23 Dec - 24 Dec
Best Western Plus Landmark Inn
Indoor pool
Lake Opechee Inn and Spa

Lake Opechee Inn and Spa

Lake Opechee Inn and Spa
3.5 star property
Lakeport
9.4 out of 10, Exceptional, (649)
"Gracious staff, clean quiet spacious room. This was our second visit and it felt like coming home"
United States
Ruth
The price is RM835
RM906 total
includes taxes & fees
17 Dec - 18 Dec
Lake Opechee Inn and Spa
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

Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

10/10 Excellent
"This was a cute little inn with welcoming staff and comfy rooms. May not be super updated but part of the charm. Only con is the walls are incredibly thin which can be hard if you have loud neighbors. Would stay here again!"
Lindsay 1-night trip
Posted 4 days ago
Fireside Inn & Suites Gilford

Frequently asked questions

What are some accommodation options with pools in Jolly Island?
Winnisquam Lake Inn: Offers a steam room, an indoor pool and spa services. The Common Man Inn & Spa: Provides a full-service spa, an indoor pool and daily. TownePlace Suites by Marriott Gilford: Features buffet, a pool and free self parking. Best Western Plus Landmark Inn: Hotel, 9-minute walk from Lake Winnipesaukee. Offers an indoor pool, an outdoor pool and 4 restaurants. Mill Falls Resort Collection at the Lake: Features a snack bar/deli, an indoor pool and buffet.
What is there to see and do in Jolly Island?
Surround yourself with nature at Lake Winnipesaukee. During your stay, visit sights such as Bank of New Hampshire Pavilion at Meadowbrook, Ellacoya State Park and Weirs Beach.
When is the best time to book a hotel with a pool in Jolly Island?
Taking the local weather in Jolly Island into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Jolly Island are January, March, November and February, with each month seeing an average of 28 cm of snowfall.