Little Bear Island holiday rentals

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

Outdoor dining
View from Gunstock (4 miles away)
Children’s area
Kitchen and Dining area
Exceptional
(155 reviews)

Stunning view from this secluded mountain gettaway

Alton Bay

8% off
AU$7,880
for 7 nights, 1 room
AU$1,126 per night
includes taxes & fees
Stunning view from this secluded mountain gettaway
Living room
Eat in kitchen
Great LARGE  private fire pit!
The lower level which walks out to firepit area
Exceptional
(51 reviews)

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

Gilford

8% off
AU$3,603
for 7 nights, 1 chalet
AU$515 per night
includes taxes & fees
1.5 miles to Gunstock. Great for larger groups or multiple families
Twilight shot of home at dusk with luxury landscape lighting
Sugar sand beach and zero entry walk in to the where the sand continues for hundreds of feet
Sunroom overlooking lake and mountain views, great for watching guests on the beach and enjoying the sunsets.
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
AU$15,625
for 7 nights, 1 home
AU$2,232 per night
includes taxes & fees
Luxury Lakefront w/Hot Tub, Beach, Mountain Views!
Location of the house boats (blue roofs)
Bar (on property)
Property grounds
Marina amenities over view
Exceptional
(26 reviews)

🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊

Laconia

8% off
AU$4,676
for 7 nights, 1 houseboat
AU$668 per night
includes taxes & fees
🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊
Interior
Exterior
Private kitchen
Dining
Exceptional
(23 reviews)

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

Laconia

8% off
AU$17,256
for 7 nights, 1 home
AU$2,465 per night
includes taxes & fees
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Property grounds
Onsite beach bar
Marina
Exterior
Exceptional
(20 reviews)

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

Laconia

8% off
AU$4,676
for 7 nights, 1 houseboat
AU$668 per night
includes taxes & fees
🌟 Unique Houseboat Experience on Lake Winnipesaukee - Dockside! 🚤🌊
Private kitchen
Exterior
Living area
Interior
Exceptional
(105 reviews)

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

Gilford

9% off
AU$20,910
for 7 nights, 1 home
AU$2,987 per night
includes taxes & fees
Winnipesaukee's Finest Waterfront Mansion w/Boathouse and Private Beach
Kitchen and dining
Marina
Sunroom
Living area
Exceptional
(18 reviews)

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

Alton Bay

8% off
AU$5,369
for 7 nights, 1 cottage
AU$767 per night
includes taxes & fees
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee
Private kitchen
Dining
Outdoor dining
Living area
Exceptional
(9 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
AU$7,980
for 7 nights, 1 home
AU$1,140 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
Living area
Exceptional
(169 reviews)

Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile

Gilford

8% off
AU$4,707
for 7 nights, 1 home
AU$672 per night
includes taxes & fees
Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile
Exterior
Living area
Private kitchen
Dining
Exceptional
(7 reviews)

Quiet Lake Retreat with Fireplace and short walk to the beach

Moultonborough

8% off
AU$3,022
for 7 nights, 1 cottage
AU$432 per night
includes taxes & fees
Quiet Lake Retreat with Fireplace and short walk to the beach
Property from end of dock
Property from the lake
Family room
Fireplace seating area - dining area and kitchen in background
Exceptional
(154 reviews)

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

Alton Bay

8% off
AU$7,916
for 7 nights, 1 home
AU$1,131 per night
includes taxes & fees
Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more
View of the house from the beach.
Comfy seats around one of two fire pits.
Exterior
Interior
Exceptional
(185 reviews)

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

Moultonborough

8% off
AU$4,878
for 7 nights, 1 home
AU$697 per night
includes taxes & fees
Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey
Dining
Private kitchen
Living area
Living area
Exceptional
(5 reviews)

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

Gilford

12% off
AU$6,471
for 7 nights, 1 home
AU$924 per night
includes taxes & fees
Updated 4BR, Game Room/Bar, Private, Near Gunstock
Awesome guest sent photo of vase and flowers they bought for dining room table.
Sunroom 4 Season
4 season sunroom :-)
Fall colors overlooking the lake from the deck October 2022
Exceptional
(25 reviews)

Kayak, walk or swim to Meredith town center

Meredith

8% off
AU$9,984
for 7 nights, 1 home
AU$1,426 per night
includes taxes & fees
Kayak, walk or swim to Meredith town center
Private kitchen
Private kitchen
Property grounds
Marina
Exceptional
(15 reviews)

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

Wolfeboro

8% off
AU$6,148
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE
Property grounds
Property grounds
Interior
Exterior
Exceptional
(5 reviews)

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

Gilford

8% off
AU$6,587
for 7 nights, 1 home
AU$941 per night
includes taxes & fees
Fabulous 4BR house mountain & Lake Views, in lovely Gilford
Interior
Private kitchen
Games room
Property grounds
Exceptional
(24 reviews)

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

Moultonborough

7% off
AU$2,376
for 7 nights, 1 home
AU$339 per night
includes taxes & fees
Pet & Kid Friendly Lake community w/ boat launch & beach
Living area
Private kitchen
Interior
Property grounds
Exceptional
(8 reviews)

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

Moultonborough

8% off
AU$2,922
for 7 nights, 1 home
AU$417 per night
includes taxes & fees
Charming 3-bedroom house in lovely Moultonborough with WiFi, AC
Cable TV!!
Property grounds
Castle in the clouds
Snowmobilers on Shannon Brook heading towards Lake Winnipsaukee.
Wonderful
(33 reviews)

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

Moultonborough

8% off
AU$2,923
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6
Property grounds
Pool
Property grounds
Exterior
Exceptional
(9 reviews)

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

Laconia

7% off
AU$2,205
for 7 nights, 1 home
AU$315 per night
includes taxes & fees
4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7
Room
Gather by the Firepit
Exterior
Living area
Wonderful
(50 reviews)

Lake House Private Waterfront - Lake & Beach life in Winnipesaukee

Laconia

8% off
AU$8,592
for 7 nights, 1 home
AU$1,227 per night
includes taxes & fees
Lake House Private Waterfront - Lake & Beach life in Winnipesaukee
Living area
Exterior
Property grounds
Private kitchen
Exceptional
(22 reviews)

Lakes Region home, close to hiking, golf and more

Gilford

8% off
AU$7,061
for 7 nights, 1 home
AU$1,009 per night
includes taxes & fees
Lakes Region home, close to hiking, golf and more
Interior
Marina
Property grounds
Interior
Wonderful
(10 reviews)

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

Laconia

8% off
AU$3,142
for 7 nights, 1 apartment
AU$449 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. Stayz 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 Stayz 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 Stayz. 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, Stayz 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 Stayz, 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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