Little Bear Island vacation rentals

We found 1,020 vacation rentals — enter your dates for availability

Experience the enchanting charm of Little Bear Island, where breathtaking views of Lake Winnipesaukee and serene oak trees create an idyllic backdrop for your getaway. This haven invites outdoor enthusiasts and relaxation seekers alike, with hiking trails, tranquil beaches, and friendly neighborhoods bursting with local charm. Choose from cozy cottages or spacious condos, many of which are pet-friendly, ensuring comfort and convenience for group travelers. Embrace the warmth of a home-like experience while enjoying the freedom and amenities of a vacation rental, making every moment unforgettable.

Holiday rentals with weekly discounts - Little Bear Island

Showing deals for:Nov 27 - Dec 4

Great LARGE  private fire pit!
Eat in kitchen
3 season porch on main level, store all your gear here
Living room
Exceptional
(51 reviews)

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

Gilford

8% off
$394
$2,761 for 7 nights
All fees included
1.5 miles to Gunstock. Great for larger groups or multiple families
Kitchen and Dining area
View from Gunstock (4 miles away)
Outdoor dining
Children's area
Exceptional
(156 reviews)

Stunning view from this secluded mountain gettaway

Alton Bay

8% off
$766
$5,365 for 7 nights
All fees included
Stunning view from this secluded mountain gettaway
Living area
Exterior
Dining
Interior
Exceptional
(24 reviews)

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

Laconia

9% off
$1,681
$11,768 for 7 nights
All fees included
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Marina
Exterior
Interior
Private kitchen
Exceptional
(107 reviews)

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

Gilford

9% off
$2,055
$14,387 for 7 nights
All fees included
Winnipesaukee's Finest Waterfront Mansion w/Boathouse and Private Beach
Marina amenities over view
Bar (on property)
Marina
Location of the house boats (blue roofs)
Exceptional
(26 reviews)

🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊

Laconia

9% off
$452
$3,162 for 7 nights
All fees included
🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊
Living area
Dining
Outdoor dining
Private kitchen
Exceptional
(9 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
$894
$6,260 for 7 nights
All fees included
Spacious Lakes Region Retreat—Game Room & Gazebo
Property from end of dock
Property from the lake
Fireplace seating area - dining area and kitchen in background
Family room
Exceptional
(154 reviews)

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

Alton Bay

8% off
$770
$5,391 for 7 nights
All fees included
Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more
Golf
sitting on deck overlooking diamond, rattlesnake island and Wolfboro neck
Living area
view from kitchen
Exceptional
(169 reviews)

Lake Winnipesaukee enjoy the panoramic views of the lake, mountains mile

Gilford

8% off
$459
$3,211 for 7 nights
All fees included
Lake Winnipesaukee enjoy the panoramic views of the lake, mountains mile
4 season sunroom :-)
Sunroom 4 Season
Fall colors overlooking the lake from the deck October 2022
Awesome guest sent photo of vase and flowers they bought for dining room table.
Exceptional
(25 reviews)

Kayak, walk or swim to Meredith town center

Meredith

9% off
$953
$6,670 for 7 nights
All fees included
Kayak, walk or swim to Meredith town center
Private kitchen
Living area
Dining
Exterior
Exceptional
(9 reviews)

Quiet Lake Retreat with Fireplace and short walk to the beach

Moultonborough

8% off
$290
$2,028 for 7 nights
All fees included
Quiet Lake Retreat with Fireplace and short walk to the beach
Dining
Private kitchen
Lobby
Living area
Exceptional
(6 reviews)

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

Gilford

12% off
$634
$4,440 for 7 nights
All fees included
Updated 4BR, Game Room/Bar, Private, Near Gunstock
Exterior
Property grounds
Property grounds
Interior
Exceptional
(5 reviews)

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

Gilford

8% off
$632
$4,424 for 7 nights
All fees included
Fabulous 4BR house mountain & Lake Views, in lovely Gilford
Exterior
Onsite beach bar
Property grounds
Marina
Exceptional
(20 reviews)

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

Laconia

9% off
$452
$3,162 for 7 nights
All fees included
🌟 Unique Houseboat Experience on Lake Winnipesaukee - Dockside! 🚤🌊
Private kitchen
Property grounds
Cable TV!!
Snowmobilers on Shannon Brook heading towards Lake Winnipsaukee.
Wonderful
(34 reviews)

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

Moultonborough

9% off
$282
$1,971 for 7 nights
All fees included
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6
Exterior detail
Private kitchen
Property grounds
Living area
Exceptional
(9 reviews)

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

Moultonborough

8% off
$281
$1,969 for 7 nights
All fees included
Charming 3-bedroom house in lovely Moultonborough with WiFi, AC
Living area
Pool
Property grounds
Exterior
Exceptional
(9 reviews)

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

Laconia

8% off
$206
$1,439 for 7 nights
All fees included
4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7
Living area
Gather by the Firepit
Room
Living area
Wonderful
(50 reviews)

Lake House Private Waterfront - Lake & Beach life in Winnipesaukee

Laconia

8% off
$824
$5,770 for 7 nights
All fees included
Lake House Private Waterfront - Lake & Beach life in Winnipesaukee
Interior
Marina
Exterior
Interior
Wonderful
(11 reviews)

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

Laconia

8% off
$300
$2,100 for 7 nights
All fees included
Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's
Dining
Terrace/patio
Private kitchen
Exterior
Exceptional
(8 reviews)

Enchanting Alton Bay~Lake Winnipesaukee Retreat • Amazing Views & Hot Tub

Alton Bay

8% off
$387
$2,711 for 7 nights
All fees included
Enchanting Alton Bay~Lake Winnipesaukee Retreat • Amazing Views & Hot Tub
Interior
Private kitchen
Living area
Interior
Exceptional
(10 reviews)

Cozy 4-Season Chalet + Lake Winni + Gunstock + Free Breakfast · Sleeps 8

Gilford

8% off
$319
$2,234 for 7 nights
All fees included
Cozy 4-Season Chalet + Lake Winni + Gunstock + Free Breakfast · Sleeps 8
Pool
Interior
Exterior detail
Living area
Excellent
(7 reviews)

Serene Condo

Laconia

8% off
$177
$1,237 for 7 nights
All fees included
Serene Condo
Private kitchen
Exterior
Interior
Living area
Exceptional
(52 reviews)

Meredith Bay - Brand New 1st Floor Apartment In Private Home

Meredith

8% off
$273
$1,912 for 7 nights
All fees included
Meredith Bay - Brand New 1st Floor Apartment In Private Home
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

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

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Little Bear Island

Why visit Little Bear Island

  • Stunning Natural Scenery: Little Bear Island is surrounded by beautiful lakes and beaches, perfect for nature lovers.
  • Outdoor Activities: Enjoy a range of activities, from hiking at Bear Campground to relaxing on Lake Winnipesaukee.
  • Charming Nearby Towns: Explore family-friendly towns with friendly locals and rich history, enhancing your getaway experience.
  • Diverse Accommodation Options: Choose from cozy vacation homes, comfortable condos, or charming cottages tailored for families or groups.
  • Memorable Romantic Getaways: The island offers a picturesque setting ideal for couples seeking relaxation and adventure together.

Popular types of accommodation around Little Bear Island

If you’re planning a getaway to Little Bear Island, you’ll find a variety of popular vacation rental options to suit your needs. Choose from cozy houses, comfortable condos, or charming cottages. Many of these accommodations feature single beds and bunk beds, perfect for families or groups. Enjoy quality time together in spacious dining areas or unwind at family-friendly campsites. Your ideal vacation experience awaits in Little Bear Island.

  • Houses: The top choice for travelers to Little Bear Island, these homes offer spacious accommodations ideal for families and groups.
  • Condos: A popular option, condos provide a blend of comfort and convenience, often featuring amenities like pools and fitness centers.
  • Cottages: Perfect for a quaint getaway, cottages offer a cozy atmosphere with charming details.
  • Cabins: These rustic retreats immerse you in nature, making them a favorite for outdoor enthusiasts.
  • Chalets: Typically offering a ski lodge feel, chalets are a great choice for a unique vacation experience.**

Top attractions near Little Bear Island

Little Bear Island, New Hampshire, is an ideal destination for outdoor enthusiasts and romantic getaways, featuring stunning scenery around its beautiful lakes and beaches. Popular attractions include Bear Campground, Lake Winnipesaukee, Acre Island, and Cow Island, offering various activities for travelers seeking adventure and relaxation. Whether you're planning a weekend escape or a longer vacation, Little Bear Island promises a memorable experience immersed in nature.

  • Lake Winnipesaukee: Located only 2 miles from Little Bear Island, this beautiful lake offers stunning scenery and a romantic atmosphere. Enjoy outdoor activities such as boating, fishing, and picnicking along its sandy beaches.
  • Weirs Beach: Just 7 miles away, Weirs Beach is a popular destination known for its vibrant beach vibes. Relax on the sandy shores or take part in various water sports while soaking up the sun.
  • Castle in the Clouds: Situated 6 miles from Little Bear Island, this historic mansion provides a glimpse into the area's rich culture. Explore its stunning architecture and breathtaking views of the surrounding landscape.

Things to do recommended for couples

For a romantic getaway at Little Bear Island, enjoy a concert at the Bank of New Hampshire Pavilion, just 6 miles away, or hit the slopes at Gunstock Mountain Resort, 7 miles from the island. Don't forget to unwind together with a treatment at Cascade Spa, 9 miles away.

Things to do recommended for families

Families visiting Little Bear Island will love the Funspot Family Fun Center, an arcade adventure just 8 miles away. Enjoy the thrilling Gunstock Mountain Coaster, located 7 miles away, and indulge in sweet treats at Kellerhaus, also 8 miles from the island.

Things to do recommended for groups

Experience the thrill of golf at Kingswood Golf Club, just 8 miles away, or catch a family-friendly flick at Barnz's Meredith Cinema, 9 miles from Little Bear Island. Don't forget to explore unique finds at Hampshire Pewter Co., located just 7 miles away for some local shopping.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Little Bear Island

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Little Bear Island with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Little Bear Island with young kids: Traveling with little ones can be a bit daunting. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Little Bear Island: For many families, a trip isn't truly finished without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Little Bear Island: If you’re seeking vacation rentals with great deals for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Little Bear Island

Little Bear Island, New Hampshire, offers a picturesque getaway perfect for outdoor enthusiasts and romantic vacations. Surrounded by stunning lake views, you can explore charming nearby towns that embody a family-friendly atmosphere with friendly locals and rich history. Whether you’re seeking a cozy vacation home on the lake or wish to delve into the natural beauty of large islands, this destination promises an unforgettable experience filled with relaxation and scenic adventures.

  • Laconia: Located 11 miles from Little Bear Island, Laconia is a vibrant city known for its stunning outdoor scenery and romantic ambiance. Visitors flock to this destination to enjoy a variety of activities, including live music concerts and theatrical performances. With its proximity to beautiful lakes and family-friendly beaches, Laconia offers a perfect backdrop for relaxation and recreation. The scenic landscape is ideal for hiking and exploring the natural beauty of the region, making it a great spot for both adventure seekers and those looking to unwind.
  • Gilford: Just 8 miles from Little Bear Island, Gilford is a picturesque city that embodies the charm of New Hampshire’s lakes region. Known for its romantic settings and outdoor experiences, travelers can enjoy concerts, theater, and skiing in the area. With its proximity to breathtaking mountains and serene beaches, Gilford provides a perfect escape for nature lovers and families alike. Whether you’re hitting the slopes in winter or lounging by the lake in summer, the scenic beauty of Gilford ensures a memorable vacation experience.
  • Meredith: Located 9 miles from Little Bear Island, Meredith is a quaint city that offers an enchanting blend of outdoor activities and stunning scenery. It’s a popular choice for those seeking romantic getaways, with ski fields and resorts providing thrilling winter sports options. The area is dotted with beautiful lakes and family-friendly beaches, perfect for summer fun. Visitors can explore charming shops and delightful eateries, making Meredith a wonderful destination for relaxation and adventure alike.

Best time to go to Little Bear Island

If you're planning a trip to Little Bear Island, Tuftonboro, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like March to April and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.8°F (-6.2°C)Light RainMostly SunnyAverageAverage
February22.5°F (-5.3°C)Light RainMostly CloudyAverageAverage
March30.2°F (-1.0°C)Light RainMostly CloudyLowSlightly Low
April42.3°F (5.7°C)Light RainMostly CloudyLowSlightly Low
May54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
June62.8°F (17.1°C)Light RainMostly SunnyHighAverage
July69.4°F (20.8°C)Light RainMostly SunnyHighSlightly High
August68.0°F (20.0°C)Light RainMostly SunnyHighSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
October49.3°F (9.6°C)Light RainMostly SunnyAverageSlightly Low
November37.2°F (2.9°C)Light RainMostly SunnyLowAverage
December27.7°F (-2.4°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can often lead to significant savings, as prices tend to vary. Additionally, if you opt for a longer stay, you may enjoy even greater discounts. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is designed to help you plan your travels with ease. It provides a dedicated space where you can create new trips, continue working on your existing plans, or review and manage your bookings. Your saved or booked properties are conveniently organized into three categories: Potential Trips, Upcoming Trips, and Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Little Bear Island getaway

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

Activities and attractions in Little Bear Island

Are you searching for things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Little Bear Island a one-of-a-kind vacation spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Little Bear Island. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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 vacation rental accommodation in Little Bear Island?
According to our data, cottages are considered the most popular vacation property type in Little Bear Island. But as you'd expect, everyone's idea of an awesome trip isn't the same. Vrbo has vacation rentals with every size, shape and budget in mind, and we'll help you find the perfect fit.
How much does it cost to rent a vacation rental in Little Bear Island?
The average price for a vacation home in Little Bear Island is determined by several factors, like season, property type and length of stay. Whether you're searching for a sprawling villa with space for the whole family or an apartment ideal for just you and the kids, just enter your dates of travel to discover stays that offer great value.
How much does it cost to rent a beach house in Little Bear Island?
Prices for beach houses in Little Bear Island may vary depending on the size and type of the property and when you're traveling. Just enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use the filters to refine your search results by ratings, amenities and more.
What are popular rental amenities in Little Bear Island?
Some of the most popular rental amenities people search for in Little Bear Island are a firepit, a barbecue grill and a fireplace. Whether you're taking a trip with family, friends or even pets, Vrbo vacation properties include the best amenities for hanging out with the people you love.
How old do you have to be to rent a vacation rental in Little Bear Island?
The minimum age is usually 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your preferred Little Bear Island stay before booking your stay.
How long can I rent a vacation rental in Little Bear Island for?
It's down to the Little Bear Island property. To look over a list of options offering extended stays, just enter your dates and guest number into Vrbo. Enjoy having the whole property to yourself, along with home comforts like a full kitchen, air conditioning and a yard where the kids can run and play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Little Bear Island?
In Little Bear Island, you'll find some great discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a weekend getaway or a longer stay, we have a variety of options to match your style.

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