Bear Island holiday homes

We found 1,045 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Bear Island

Showing deals for:25 Dec - 1 Jan

3 season porch on main level, store all your gear here
Eat in kitchen
The lower level which walks out to firepit area
Great LARGE  private fire pit!
Exceptional
(53 reviews)

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

Gilford

8% off
NZ$6,261
for 7 nights, 1 chalet
NZ$894 per night
includes taxes & fees
1.5 miles to Gunstock. Great for larger groups or multiple families
Interior
Exterior
Dining
Private kitchen
Exceptional
(26 reviews)

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

Laconia

8% off
NZ$25,773
for 7 nights, 1 home
NZ$3,682 per night
includes taxes & fees
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Winter Sunrise - view from the enclosed porch
Back of house from dock
Living area
Porch
Exceptional
(39 reviews)

Gorgeous Waterfront with Dock & Mountain Views on Winnisquam - Sleeps 10

Sanbornton

8% off
NZ$13,077
for 7 nights, 1 home
NZ$1,868 per night
includes taxes & fees
Gorgeous Waterfront with Dock & Mountain Views on Winnisquam - Sleeps 10
Exterior
Gather by the Firepit
Living area
Living area
Wonderful
(51 reviews)

Lake House Private Waterfront - Lake & Beach life in Winnipesaukee

Laconia

8% off
NZ$10,779
for 7 nights, 1 home
NZ$1,540 per night
includes taxes & fees
Lake House Private Waterfront - Lake & Beach life in Winnipesaukee
Private kitchen
Dining
Living area
Outdoor dining
Exceptional
(10 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
NZ$16,110
for 7 nights, 1 home
NZ$2,301 per night
includes taxes & fees
Spacious Lakes Region Retreat—Game Room & Gazebo
Living area
sitting on deck overlooking diamond, rattlesnake island and Wolfboro neck
view from kitchen
Golf
Exceptional
(171 reviews)

Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile

Gilford

8% off
NZ$5,949
for 7 nights, 1 home
NZ$850 per night
includes taxes & fees
Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile
Dining
Living area
Exterior
Room
Exceptional
(10 reviews)

Quiet Lake Retreat with Fireplace and short walk to the beach

Moultonborough

8% off
NZ$5,353
for 7 nights, 1 cottage
NZ$765 per night
includes taxes & fees
Quiet Lake Retreat with Fireplace and short walk to the beach
Master Bedroom
Property from the lake
Property from end of dock
Family room
Exceptional
(157 reviews)

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

Alton Bay

8% off
NZ$9,946
for 7 nights, 1 home
NZ$1,421 per night
includes taxes & fees
Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more
4 season sunroom :-)
Sunroom 4 Season
Fall colors overlooking the lake from the deck October 2022
Private kitchen
Exceptional
(26 reviews)

Kayak, walk or swim to Meredith town center

Meredith

8% off
NZ$12,866
for 7 nights, 1 home
NZ$1,838 per night
includes taxes & fees
Kayak, walk or swim to Meredith town center
Private kitchen
Interior
Exterior detail
Dining area
Exceptional
(28 reviews)

Easiest Location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith

Meredith

8% off
NZ$11,674
for 7 nights, 1 home
NZ$1,668 per night
includes taxes & fees
Easiest Location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith
Marina
Private kitchen
Living area
Property grounds
Exceptional
(16 reviews)

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

Wolfeboro

8% off
NZ$10,214
for 7 nights, 1 home
NZ$1,459 per night
includes taxes & fees
NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE
View of the house from the beach.
Comfy seats around one of two fire pits.
12c coffee pot, keurig, 4 slice toaster, blender, etc.
Exterior
Exceptional
(188 reviews)

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

Moultonborough

8% off
NZ$5,230
for 7 nights, 1 home
NZ$747 per night
includes taxes & fees
Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey
Castle in the clouds
Property grounds
Snowmobilers on Shannon Brook heading towards Lake Winnipsaukee.
Cable TV!!
Wonderful
(36 reviews)

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

Moultonborough

8% off
NZ$3,620
for 7 nights, 1 home
NZ$517 per night
includes taxes & fees
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6
Property grounds
Pool
Exterior
Living area
Exceptional
(10 reviews)

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

Laconia

8% off
NZ$2,736
for 7 nights, 1 home
NZ$391 per night
includes taxes & fees
4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7
Interior
Private kitchen
Interior
Living area
Exceptional
(10 reviews)

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

Gilford

8% off
NZ$5,127
for 7 nights, 1 home
NZ$732 per night
includes taxes & fees
Cozy 4-Season Chalet + Lake Winni + Gunstock + Free Breakfast · Sleeps 8
Dining
Exterior
Interior
Private kitchen
Exceptional
(53 reviews)

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

Meredith

8% off
NZ$3,999
for 7 nights, 1 home
NZ$571 per night
includes taxes & fees
Meredith Bay - Brand New 1st Floor Apartment In Private Home
Interior
Marina
Property grounds
Exterior
Wonderful
(12 reviews)

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

Laconia

8% off
NZ$3,891
for 7 nights, 1 apartment
NZ$556 per night
includes taxes & fees
Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's
  • Peace of mind

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  • All the privacy of home

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

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Bear Island getaway

Learn about the unique charm of Bear Island with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Bear Island

Are you looking for top things to see and do in the city? Venture out of your holiday home and experience everything that 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:

  • Ellacoya State Park (5.1 mi / 8.2 km)
  • Gunstock Mountain Resort (6.9 mi / 11.2 km)
  • Squam Lakes Natural Science Center (11.6 mi / 18.6 km)
  • Stand Up Paddleboard NH (15 mi / 24.1 km)
  • Sandwich Creamery (15.4 mi / 24.8 km)
  • Kellerhaus (4 mi / 6.5 km)

Exploring the natural landscape of Bear Island

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Bear Island is a great place to get out in nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Weirs Beach (3.7 mi / 5.9 km)
  • Lake Winnipesaukee (4.3 mi / 7 km)
  • Ellacoya State Park (5.1 mi / 8.2 km)
  • Paugus Bay (5.6 mi / 9 km)
  • Lake Waukewan (6.4 mi / 10.3 km)
  • Opechee Park Cove Beach and Opechee Point Beach (8 mi / 12.9 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Bear Island?
The most in-demand types of holiday homes in Bear Island are houses. Looking for something different? Bookabach has many options to match our guests' needs, so you'll see properties in all shapes and sizes. The perfect fit is waiting for you — snap up yours today.
How much does it cost to rent a holiday home in Bear Island?
The average price for a holiday home in Bear Island is based on several factors, such as length of stay, property type and season. Whether you're in search of a sprawling villa with room to move around or an apartment ideal for just you and the kids, just add your dates of travel to discover some great-value stays.
How much does it cost to rent a beach house in Bear Island?
The average price for a holiday home by the beach in Bear Island will depend on when you'll be there and the size and style of property you're looking for. Find prices easily and quickly on Bookabach by entering your preferred travel dates and destination. Then use the handy filters to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a pool.
What are popular home amenities in Bear Island?
Mountain views, a nearby waterfront and a lake view rank as the most popular home amenities in Bear Island. Whether you're taking to the road solo, with your sweetheart or a bunch of friends, Bookabach will help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there holiday homes with WiFi in Bear Island?
Whether you'd like to keep up with the headlines, send a few emails or surf your social networks, there are three holiday homes with WiFi in Bear Island. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How old do you have to be to rent a holiday home in Bear Island?
Age restrictions can vary across properties on Bookabach, so be sure to check the rules of the holiday home in Bear Island you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Bear Island for?
The length of time you can rent a holiday home in Bear Island is up to the property. Just enter your selected travel dates to see a list of options offering extended stays. With plenty of creature comforts like air conditioning and full kitchens, as well as some offering discounted weekly or monthly prices, you're sure to discover somewhere just right to call your home away from home in Bear Island.

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