Search Vacation Homes in Little Bear Island

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Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
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Jan 2 - Jan 4
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Jan 30 - Feb 1

Vacation Homes in Little Bear Island

Exterior
Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 star property
Ashland
9.2 out of 10, Wonderful, (159)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
$103 nightly
The price is $112
Dec 18 - Dec 19
Total with taxes and fees
Cold Spring Plymouth Resort
Outdoor dining
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.
$398 nightly
The price is $432
Dec 5 - Dec 6
Total with taxes and fees
Mountainside chalet with a sauna and beautiful views near Lake Winnipesaukee NH!
Exterior
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

Freedom
8.8 out of 10, Excellent, (31)
"It was great and the weather was perfect. Love that it’s dog friendly! And Helen was very helpful. "
United States
ELIZABETH B T.
$283 nightly
The price is $307
Dec 17 - Dec 18
Total with taxes and fees
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
Smart TV, fireplace
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Sanbornton
10.0 out of 10, Exceptional, (13)
"Great location, great kitchen, great bedding"
United States
Wanaka G.
$640 nightly
The price is $694
Dec 5 - Dec 6
Total with taxes and fees
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
TV, stereo
Stay in Venice our Modern Steps from the Lake with Dock!

Stay in Venice our Modern Steps from the Lake with Dock!

Alton
10.0 out of 10, Exceptional, (7)
"Very clean and in a great location."
United States
Mark B.
$347 nightly
The price is $378
Dec 7 - Dec 8
Total with taxes and fees
Stay in Venice our Modern Steps from the Lake with Dock!
Terrace/patio
3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!

3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!

Laconia
9.2 out of 10, Wonderful, (5)
$271 nightly
The price is $294
Dec 5 - Dec 6
Total with taxes and fees
3-bedroom + double futon, 2 bath house in Laconia, 1 mile from Lake Winnisquam!
Terrace/patio
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.
$340 nightly
The price is $369
Dec 8 - Dec 9
Total with taxes and fees
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
Property grounds
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, (16)
"We arrived super late and while it was very dark out the house was very easy to find. Entry process exactly as described.It was warm evening and they had on numerous fans and the a/c making it feel uber pleasant.Hade writhing we needed. "
United States
Monte J.
$319 nightly
The price is $346
Dec 5 - Dec 6
Total with taxes and fees
Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Fridge, microwave, oven, stovetop
19 Mile Bay - Tuftonboro - Lake Winnipesaukee

19 Mile Bay - Tuftonboro - Lake Winnipesaukee

Tuftonboro
10.0 out of 10, Exceptional, (18)
"My stay there with my family was amazing with near by beaches and great views of the lakes. The house was very clean when we arrived and the back yard with cornhole boards was a plus over all this house and location was awesome!!"
United States
Oudom S.
$706 nightly
The price is $766
Dec 29 - Dec 30
Total with taxes and fees
19 Mile Bay - Tuftonboro - Lake Winnipesaukee
Pool
New Home Private Pool/Hot Tub Near Meredith Center

New Home Private Pool/Hot Tub Near Meredith Center

Meredith
9.6 out of 10, Exceptional, (51)
"We enjoyed staying in this beautiful home."
United States
D M.
New Home Private Pool/Hot Tub Near Meredith Center
Exterior
A four-season lakefront getaway on your own private peninsula

A four-season lakefront getaway on your own private peninsula

2.0 star property
The Bays
10.0 out of 10, Exceptional, (1)
"This property is so beautiful! The hosts weee amazing. Cant wait to book this property again! "
United States
Deanna B.
$621 nightly
The price is $674
Dec 14 - Dec 15
Total with taxes and fees
A four-season lakefront getaway on your own private peninsula
Fridge, microwave, oven, stovetop
Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway

Gilford
10.0 out of 10, Exceptional, (72)
"Beautiful property. We enjoyed our trip."
United States
DEBORAH
$577 nightly
The price is $626
Dec 5 - Dec 6
Total with taxes and fees
Idyllic Mountain and Lake Getaway
Smart TV, fireplace, video games, table tennis
Baby Chocorua A Frame in the mountains sleeps 9

Baby Chocorua A Frame in the mountains sleeps 9

Chocorua
10.0 out of 10, Exceptional, (18)
"Beautiful house with great amenities. "
United States
Bill P.
$452 nightly
The price is $490
Dec 8 - Dec 9
Total with taxes and fees
Baby Chocorua A Frame in the mountains sleeps 9
Terrace/patio
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, (3)
"Place was clean and nice. "
United States
Bryan K.
$817 nightly
The price is $886
Dec 10 - Dec 11
Total with taxes and fees
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
Outdoor dining
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

Gilford
10.0 out of 10, Exceptional, (2)
"We had a great time at the Wagner Ranch. The bedrooms were comfy and the kitchen had all necessary items. Definitely will stay there again. The hosts were Great!"
United States
dave b.
$553 nightly
The price is $600
Jan 4 - Jan 5, 2026
Total with taxes and fees
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location
Marina
Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake

Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake

Alton
9.6 out of 10, Exceptional, (4)
"My brothers and I had an incredible time on the lake and experienced the local amenities. The individual apartments were perfect for our needs and allowed for everyone to have their own space. The property was well managed and maintained. I would highly recommend this location for anyone looking to enjoy lake Winni! Thank you, Ron"
United States
Ronnie G.
$1,029 nightly
The price is $1,121
Dec 7 - Dec 8
Total with taxes and fees
Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake
Property grounds
Melvin Village - 5 Bed/3 Bath - Lake Winnipesaukee

Melvin Village - 5 Bed/3 Bath - Lake Winnipesaukee

Tuftonboro
10.0 out of 10, Exceptional, (22)
"The house was perfect for our large family (11 people and two dogs!) and the location was exactly what we wanted. The house was clean and had everything we needed (and didn’t know we needed)."
United States
Shayla N.
$948 nightly
The price is $1,029
Dec 28 - Dec 29
Total with taxes and fees
Melvin Village - 5 Bed/3 Bath - Lake Winnipesaukee
Exterior
Waterfront Retreat on Lake Winnisquam

Waterfront Retreat on Lake Winnisquam

Meredith
$1,564 nightly
The price is $1,697
Jan 1 - Jan 2, 2026
Total with taxes and fees
Waterfront Retreat on Lake Winnisquam
Terrace/patio
New Lakefront Home sleeps 14 with dock.

New Lakefront Home sleeps 14 with dock.

Alton
8.6 out of 10, Excellent, (67)
"We had such a nice time! The lake is gorgeous and everything we hoped for."
United States
Kirby L.
$847 nightly
The price is $923
Dec 26 - Dec 27
Total with taxes and fees
New Lakefront Home sleeps 14 with dock.
Terrace/patio
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)
"Perfect waterfront stay but did not like being so close to the road."
United States
Lucas T.
$414 nightly
The price is $451
Dec 7 - Dec 8
Total with taxes and fees
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
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 Little Bear Island Hotel Reviews

Super 8 by Wyndham Tilton/Lake Winnipesaukee

Super 8 by Wyndham Tilton/Lake Winnipesaukee

10/10 Excellent
"Very convenient location, nice continental breakfast. "
Catherine 1-night trip
Posted 1 day ago
Super 8 by Wyndham Tilton/Lake Winnipesaukee

Find out more about Little Bear Island

Little Bear Island Vacation Homes information

Number of reviews
159
Accommodation
779 Vacation Homes
Lowest Price
$112
Highest Price
$112

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