Little Bear Island holiday homes

We found 1,021 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Little Bear Island

Showing deals for:13 Nov - 20 Nov

Kitchen and Dining area
View from Gunstock (4 miles away)
Living area with wood burning fireplace and puzzle table
Outdoor dining
Exceptional
(155 reviews)

Stunning view from this secluded mountain gettaway

Alton Bay

8% off
NZ$9,668
for 7 nights, 1 room
NZ$1,381 per night
includes taxes & fees
Stunning view from this secluded mountain gettaway
Great LARGE  private fire pit!
Eat in kitchen
The lower level which walks out to firepit area
3 season porch on main level, store all your gear here
Exceptional
(51 reviews)

1.5 miles to Gunstock. Great for larger groups or multiple families

Gilford

7% off
NZ$4,450
for 7 nights, 1 chalet
NZ$636 per night
includes taxes & fees
1.5 miles to Gunstock. Great for larger groups or multiple families
Sunroom overlooking lake and mountain views, great for watching guests on the beach and enjoying the sunsets.
Sugar sand beach and zero entry walk in to the where the sand continues for hundreds of feet
Twilight shot of home at dusk with luxury landscape lighting
Living room with massive couch, 85" tv, sound system, pool table, and bubble hockey game
Exceptional
(64 reviews)

Luxury Lakefront w/Hot Tub, Beach, Mountain Views!

Moultonborough

9% off
NZ$18,867
for 7 nights, 1 home
NZ$2,695 per night
includes taxes & fees
Luxury Lakefront w/Hot Tub, Beach, Mountain Views!
Property grounds
Bar (on property)
Marina
Location of the house boats (blue roofs)
Exceptional
(26 reviews)

🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊

Laconia

8% off
NZ$5,737
for 7 nights, 1 houseboat
NZ$820 per night
includes taxes & fees
🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊
Interior
Exterior
Living area
Private kitchen
Exceptional
(23 reviews)

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

Laconia

8% off
NZ$20,881
for 7 nights, 1 home
NZ$2,983 per night
includes taxes & fees
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Exterior
Onsite beach bar
Property grounds
Pool
Exceptional
(20 reviews)

🌟 Unique Houseboat Experience on Lake Winnipesaukee - Dockside! 🚤🌊

Laconia

8% off
NZ$5,737
for 7 nights, 1 houseboat
NZ$820 per night
includes taxes & fees
🌟 Unique Houseboat Experience on Lake Winnipesaukee - Dockside! 🚤🌊
Living area
Exterior
Private kitchen
Marina
Exceptional
(105 reviews)

Winnipesaukee's Finest Waterfront Mansion w/Boathouse and Private Beach

Gilford

9% off
NZ$25,384
for 7 nights, 1 home
NZ$3,626 per night
includes taxes & fees
Winnipesaukee's Finest Waterfront Mansion w/Boathouse and Private Beach
Living area
Marina
Kitchen and dining
Living area
Exceptional
(18 reviews)

The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

Alton Bay

8% off
NZ$6,578
for 7 nights, 1 cottage
NZ$940 per night
includes taxes & fees
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee
Living area
Dining
Outdoor dining
Living area
Exceptional
(9 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
NZ$9,789
for 7 nights, 1 home
NZ$1,398 per night
includes taxes & fees
Spacious Lakes Region Retreat—Game Room & Gazebo
view from kitchen
sitting on deck overlooking diamond, rattlesnake island and Wolfboro neck
Golf
Private kitchen
Exceptional
(169 reviews)

Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile

Gilford

8% off
NZ$5,773
for 7 nights, 1 home
NZ$825 per night
includes taxes & fees
Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile
Master Bedroom
Property from the lake
Family room
Property from end of dock
Exceptional
(154 reviews)

Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more

Alton Bay

8% off
NZ$9,714
for 7 nights, 1 home
NZ$1,388 per night
includes taxes & fees
Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more
Exterior
Living area
Private kitchen
Room
Exceptional
(7 reviews)

Quiet Lake Retreat with Fireplace and short walk to the beach

Moultonborough

8% off
NZ$3,662
for 7 nights, 1 cottage
NZ$523 per night
includes taxes & fees
Quiet Lake Retreat with Fireplace and short walk to the beach
Interior
Comfy seats around one of two fire pits.
12c coffee pot, keurig, 4 slice toaster, blender, etc.
View of the house from the beach.
Exceptional
(185 reviews)

Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey

Moultonborough

8% off
NZ$5,983
for 7 nights, 1 home
NZ$855 per night
includes taxes & fees
Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey
Living area
Private kitchen
Living area
Dining
Exceptional
(5 reviews)

Updated 4BR, Game Room/Bar, Private, Near Gunstock

Gilford

12% off
NZ$7,892
for 7 nights, 1 home
NZ$1,127 per night
includes taxes & fees
Updated 4BR, Game Room/Bar, Private, Near Gunstock
Fall colors overlooking the lake from the deck October 2022
Sunroom 4 Season
4 season sunroom :-)
Private kitchen
Exceptional
(25 reviews)

Kayak, walk or swim to Meredith town center

Meredith

8% off
NZ$12,582
for 7 nights, 1 home
NZ$1,797 per night
includes taxes & fees
Kayak, walk or swim to Meredith town center
Marina
Private kitchen
Property grounds
Private kitchen
Exceptional
(15 reviews)

NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE

Wolfeboro

8% off
NZ$7,505
for 7 nights, 1 home
NZ$1,072 per night
includes taxes & fees
NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE
Interior
Property grounds
Exterior
Private kitchen
Exceptional
(5 reviews)

Fabulous 4BR house mountain & Lake Views, in lovely Gilford

Gilford

8% off
NZ$8,032
for 7 nights, 1 home
NZ$1,147 per night
includes taxes & fees
Fabulous 4BR house mountain & Lake Views, in lovely Gilford
Games room
Private kitchen
Interior
Children’s area
Exceptional
(24 reviews)

Pet & Kid Friendly Lake community w/ boat launch & beach

Moultonborough

7% off
NZ$2,853
for 7 nights, 1 home
NZ$408 per night
includes taxes & fees
Pet & Kid Friendly Lake community w/ boat launch & beach
Interior
Private kitchen
Exterior detail
Living area
Exceptional
(8 reviews)

Charming 3-bedroom house in lovely Moultonborough with WiFi, AC

Moultonborough

8% off
NZ$3,538
for 7 nights, 1 home
NZ$505 per night
includes taxes & fees
Charming 3-bedroom house in lovely Moultonborough with WiFi, AC
Snowmobilers on Shannon Brook heading towards Lake Winnipsaukee.
Property grounds
Castle in the clouds
Private kitchen
Wonderful
(33 reviews)

Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6

Moultonborough

8% off
NZ$3,540
for 7 nights, 1 home
NZ$506 per night
includes taxes & fees
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6
Property grounds
Pool
Property grounds
Living area
Exceptional
(9 reviews)

4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7

Laconia

7% off
NZ$2,611
for 7 nights, 1 home
NZ$373 per night
includes taxes & fees
4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7
Living area
Gather by the Firepit
Room
Exterior
Wonderful
(50 reviews)

Lake House Private Waterfront - Lake & Beach life in Winnipesaukee

Laconia

8% off
NZ$10,541
for 7 nights, 1 home
NZ$1,506 per night
includes taxes & fees
Lake House Private Waterfront - Lake & Beach life in Winnipesaukee
Private kitchen
Exterior
Property grounds
Interior
Exceptional
(22 reviews)

Lakes Region home, close to hiking, golf and more

Gilford

8% off
NZ$8,674
for 7 nights, 1 home
NZ$1,239 per night
includes taxes & fees
Lakes Region home, close to hiking, golf and more
Interior
Marina
Interior
Exterior
Wonderful
(10 reviews)

Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's

Laconia

8% off
NZ$3,805
for 7 nights, 1 apartment
NZ$544 per night
includes taxes & fees
Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Little Bear Island getaway

Learn about the unique charm of Little Bear Island with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Little Bear Island

Are you hoping to discover top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that Little Bear Island has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Wolfeboro Abenaki Ski Area (5.1 mi / 8.1 km)
  • Gunstock Mountain Resort (7.2 mi / 11.6 km)
  • Cascade Spa (8.7 mi / 14 km)
  • Stand Up Paddleboard NH (11.9 mi / 19.1 km)
  • Squam Lakes Natural Science Center (14.7 mi / 23.7 km)
  • Ellacoya State Park (5 mi / 8 km)

Exploring the natural features in Little Bear Island

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Little Bear Island is a great place to get out in nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Winnipesaukee (2.2 mi / 3.5 km)
  • Mirror Lake (3.1 mi / 5.1 km)
  • Weirs Beach (7.1 mi / 11.4 km)
  • Paugus Bay (8.4 mi / 13.4 km)
  • Mount Major (9.1 mi / 14.6 km)
  • Lake Wentworth (9.3 mi / 14.9 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Little Bear Island?
Based on our research, houses are the most popular holiday home type in Little Bear Island. But as you'd expect, everyone's idea of an epic trip can vary. Bookabach has holiday homes of all shapes and sizes, and we'll help you find the perfect match.
How much does it cost to rent a holiday home in Little Bear Island?
A range of things affect what you'll pay for your holiday home in Little Bear Island, such as the length of stay, type of property and season. But, all Bookabach homes have one thing in common — incredible value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Little Bear Island?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Click on your Little Bear Island travel dates to view your available options on Bookabach. Can't live without a private pool? Use our filters to pick the amenities and features you want in your holiday home.
What are popular home amenities in Little Bear Island?
The most popular home amenities people prefer in Little Bear Island include mountain views, a nearby waterfront and nearby museums. Whether you're travelling with family, your besties or even pets, Bookabach holiday homes come with the best amenities for fun and relaxation with the people closest to you.
How old do you have to be to rent a holiday home in Little Bear Island?
The age limit can differ across properties on Bookabach, so look at the rules of the holiday home in Little Bear Island you're considering. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Little Bear Island for?
How long you can book a holiday home in Little Bear Island is down to the property. Just enter your desired travel dates to view a list of options offering extended stays. With lots of amenities like kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get the perfect place to call your home away from home in Little Bear Island.

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