Bear Island holiday rentals

We found 1,044 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Bear Island

Showing deals for:18 Dec - 25 Dec

3 season porch on main level, store all your gear here
Eat in kitchen
Living room
The lower level which walks out to firepit area
Exceptional
(53 reviews)

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

Gilford

8% off
AU$4,945
for 7 nights, 1 chalet
AU$706 per night
includes taxes & fees
1.5 miles to Gunstock. Great for larger groups or multiple families
Dining
Exterior
Private kitchen
Interior
Exceptional
(25 reviews)

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

Laconia

8% off
AU$19,493
for 7 nights, 1 home
AU$2,785 per night
includes taxes & fees
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Porch
Back of house from dock
First floor  en suite
Winter Sunrise - view from the enclosed porch
Exceptional
(39 reviews)

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

Sanbornton

8% off
AU$10,065
for 7 nights, 1 home
AU$1,438 per night
includes taxes & fees
Gorgeous Waterfront with Dock & Mountain Views on Winnisquam - Sleeps 10
Room
Gather by the Firepit
Living area
Exterior
Wonderful
(51 reviews)

Lake House Private Waterfront - Lake & Beach life in Winnipesaukee

Laconia

8% off
AU$8,520
for 7 nights, 1 home
AU$1,217 per night
includes taxes & fees
Lake House Private Waterfront - Lake & Beach life in Winnipesaukee
Living area
Dining
Living area
Private kitchen
Exceptional
(10 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
AU$10,550
for 7 nights, 1 home
AU$1,507 per night
includes taxes & fees
Spacious Lakes Region Retreat—Game Room & Gazebo
Golf
sitting on deck overlooking diamond, rattlesnake island and Wolfboro neck
Living area
Private kitchen
Exceptional
(170 reviews)

Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile

Gilford

8% off
AU$4,699
for 7 nights, 1 home
AU$671 per night
includes taxes & fees
Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile
Master Bedroom
Property from the lake
Fireplace seating area - dining area and kitchen in background
Property from end of dock
Exceptional
(157 reviews)

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

Alton Bay

8% off
AU$7,863
for 7 nights, 1 home
AU$1,123 per night
includes taxes & fees
Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more
Private kitchen
Living area
Exterior
Dining
Exceptional
(10 reviews)

Quiet Lake Retreat with Fireplace and short walk to the beach

Moultonborough

8% off
AU$3,519
for 7 nights, 1 cottage
AU$503 per night
includes taxes & fees
Quiet Lake Retreat with Fireplace and short walk to the beach
Awesome guest sent photo of vase and flowers they bought for dining room table.
Sunroom 4 Season
Private kitchen
4 season sunroom :-)
Exceptional
(26 reviews)

Kayak, walk or swim to Meredith town center

Meredith

8% off
AU$9,901
for 7 nights, 1 home
AU$1,414 per night
includes taxes & fees
Kayak, walk or swim to Meredith town center
Private kitchen
Interior
Dining area
Exterior detail
Exceptional
(28 reviews)

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

Meredith

8% off
AU$9,224
for 7 nights, 1 home
AU$1,318 per night
includes taxes & fees
Easiest Location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith
Private kitchen
Private kitchen
Living area
Marina
Exceptional
(16 reviews)

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

Wolfeboro

8% off
AU$6,403
for 7 nights, 1 home
AU$915 per night
includes taxes & fees
NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE
Interior
Comfy seats around one of two fire pits.
View of the house from the beach.
12c coffee pot, keurig, 4 slice toaster, blender, etc.
Exceptional
(188 reviews)

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

Moultonborough

8% off
AU$4,107
for 7 nights, 1 home
AU$587 per night
includes taxes & fees
Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey
Private kitchen
Property grounds
Cable TV!!
Snowmobilers on Shannon Brook heading towards Lake Winnipsaukee.
Wonderful
(36 reviews)

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

Moultonborough

8% off
AU$2,899
for 7 nights, 1 home
AU$414 per night
includes taxes & fees
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6
Interior
Property grounds
Property grounds
Exterior
Exceptional
(5 reviews)

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

Gilford

8% off
AU$6,580
for 7 nights, 1 home
AU$940 per night
includes taxes & fees
Fabulous 4BR house mountain & Lake Views, in lovely Gilford
Property grounds
Pool
Property grounds
Living area
Exceptional
(10 reviews)

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

Laconia

7% off
AU$2,171
for 7 nights, 1 home
AU$310 per night
includes taxes & fees
4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7
Private kitchen
Exterior
Living area
Interior
Exceptional
(24 reviews)

Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct

Gilford

8% off
AU$6,471
for 7 nights, 1 home
AU$924 per night
includes taxes & fees
Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct
Interior
Marina
Property grounds
Interior
Wonderful
(12 reviews)

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

Laconia

8% off
AU$3,078
for 7 nights, 1 apartment
AU$440 per night
includes taxes & fees
Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's
Interior
Private kitchen
Interior
Living area
Exceptional
(10 reviews)

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

Gilford

8% off
AU$3,790
for 7 nights, 1 home
AU$541 per night
includes taxes & fees
Cozy 4-Season Chalet + Lake Winni + Gunstock + Free Breakfast · Sleeps 8
Private kitchen
Exterior
Living area
Dining
Exceptional
(53 reviews)

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

Meredith

8% off
AU$2,774
for 7 nights, 1 home
AU$396 per night
includes taxes & fees
Meredith Bay - Brand New 1st Floor Apartment In Private Home
  • 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

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? Stayz 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 Stayz 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, Stayz 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 Stayz 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 Stayz, 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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