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Little Bear Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Little Bear Island vacation rentals

A row of brown single-story buildings with a parking lot in front.

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (271 reviews)
"Had a great weekend stay."
United States
Armand
The price is ￥20,837
￥22,608 total
includes taxes & fees
Oct 25 - Oct 26
Cold Spring Plymouth Resort
A spacious kitchen with wooden beams, a large dining table, and a fireplace.

2. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (2 reviews)
"We’ll kept "
United States
Denise
The price is ￥33,362
￥72,752 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Tuftonboro Escape: Steps to Private Beaches!
A modern kitchen with white cabinets, a built-in microwave, and a dishwasher. There are two bar stools near the kitchen counter.

3. 9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
8.0 out of 10, Very good, (2 reviews)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is ￥36,051
￥56,784 total
includes taxes & fees
Oct 4 - Oct 5
9 Lake Street
A beach with a picnic table, a grill, and a fire pit.

4. Experience Winter at Gunstock Ski Resorts and Relax in the Scenic Lake Region.

Experience Winter at Gunstock Ski Resorts and Relax in the Scenic Lake Region.
Gilford
9.8 out of 10, Exceptional, (50 reviews)
"Beautiful property, great amenities, and a communcative host throughout our stay. The downstairs game room is pretty nice and has a Wii if you bring your own games."
United States
Justin C.
The price is ￥66,882
￥123,963 total
includes taxes & fees
Oct 4 - Oct 5
Experience Winter at Gunstock Ski Resorts and Relax in the Scenic Lake Region.
A lake with a sandy beach and a concrete dock extending into the water.

5. Private Pond Cabin with Lake Access & Fire Pit

Private Pond Cabin with Lake Access & Fire Pit
Tuftonboro
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful property "
United States
Keith B.
Private Pond Cabin with Lake Access & Fire Pit
A covered outdoor seating area with a view of a lake, a sofa, a table, and string lights.

6. Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain

Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
Moultonborough
9.8 out of 10, Exceptional, (103 reviews)
"Great location, very quiet and relaxing"
United States
Thiago S.
The price is ￥92,061
￥141,891 total
includes taxes & fees
Oct 12 - Oct 13
Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
A waterfront town with a large ferry dock, residential buildings, and a marina.

7. 2 Bdrm Condo walking distance to Weirs Beach and much more!!

2 Bdrm Condo walking distance to Weirs Beach and much more!!
Weirs Beach
9.6 out of 10, Exceptional, (60 reviews)
"Great location, easy and smooth stay!"
United States
Aimee M.
2 Bdrm Condo walking distance to Weirs Beach and much more!!
A serene lakeside view at sunset with a silhouette of trees and a calm water surface.

8. Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (22 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is ￥23,992
￥29,789 total
includes taxes & fees
Oct 25 - Oct 26
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A spacious kitchen with a large island, a fireplace, and a deck with outdoor seating.

9. Cozy, Pet-Friendly Escape Near Lake & Mountains

Cozy, Pet-Friendly Escape Near Lake & Mountains
Gilford
10.0 out of 10, Exceptional, (49 reviews)
"Cute and comfortable. The host communicated well and had all the essentials available. We enjoyed our stay."
United States
Julie W.
The price is ￥30,038
￥75,808 total
includes taxes & fees
Oct 4 - Oct 5
Cozy, Pet-Friendly Escape Near Lake & Mountains
A spacious living area with a dining table, chairs, and a sofa.

10. Spacious Lakes Region Retreat—Game Room & Gazebo

Spacious Lakes Region Retreat—Game Room & Gazebo
Meredith
9.6 out of 10, Exceptional, (10 reviews)
"House was immaculate with all the amenities we needed. Beautiful home."
United States
Bernadette M.
The price is ￥104,494
￥207,628 total
includes taxes & fees
Oct 14 - Oct 15
Spacious Lakes Region Retreat—Game Room & Gazebo
A two-story house with a balcony, a covered porch, and a staircase leading to the entrance.

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

Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct
Gilford
9.6 out of 10, Exceptional, (24 reviews)
"This house was great!!! Plenty of space, clean & owner is very responsive!! We stayed for a concert at the pavilion & the distance was perfect. Wish we were staying longer!"
United States
Marie S.
Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct
A beach with picnic tables and lounge chairs, a stone wall, and a view of the lake and distant mountains.

12. Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.8 out of 10, Exceptional, (35 reviews)
"Great location, specially for concerts or enjoying the beach. Some road noise."
United States
Estuardo
The price is ￥18,098
￥38,589 total
includes taxes & fees
Oct 19 - Oct 20
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
A kitchen with a granite countertop, white cabinets, a built-in stove, and a hanging light fixture.

13. Lake Winni Waterfront Condo

Lake Winni Waterfront Condo
Gilford
9.8 out of 10, Exceptional, (6 reviews)
"I liked that it was close to the pavilion and had a nice view. The property looked nice for early season. It was loud this weekend due to bike week. I had a small issue with the entry as I didn’t see at first the electronic key pad and was trying to open the master lock key box. As I was only able to communicate by e mail there was no short term communication help available"
United States
robert
The price is ￥31,133
￥60,462 total
includes taxes & fees
Nov 1 - Nov 2
Lake Winni Waterfront Condo
A cozy lounge area with stone walls, wicker furniture, and a self-storage sign.

14. Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
Laconia
10.0 out of 10, Exceptional, (32 reviews)
"Easy process and great location"
United States
Daniel
The price is ￥24,078
￥54,641 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
A waterfront town with a large ferry dock, residential buildings, and a marina.

15. Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!

Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!
Weirs Beach
9.6 out of 10, Exceptional, (77 reviews)
"Nice clean place. Easy to get in and out. 10 minute drive to Bank of New Hampshire Pavillion."
United States
Kevin G.
The price is ￥35,327
￥70,834 total
includes taxes & fees
Oct 5 - Oct 6
Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!
A lakeside view with a boat on the water, a table with chairs, and a tent.

16. Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
Meredith
10.0 out of 10, Exceptional, (176 reviews)
"We loved our stay. Very clean and in a great location in Meredith."
United States
Rebecca R.
The price is ￥35,566
￥63,177 total
includes taxes & fees
Oct 7 - Oct 8
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
A spacious living room with a wooden ceiling, large windows, a sofa, a coffee table, and a fireplace.

17. Gunstock Chalet - 4BR, Skiing, Concerts, Hiking, & Fall Foliage

Gunstock Chalet - 4BR, Skiing, Concerts, Hiking, & Fall Foliage
Gilford
10.0 out of 10, Exceptional, (4 reviews)
"Very clean, well represented on site. Check-in process was very easy and smooth.Definitely on our list for future stays."
United States
Brian B.
The price is ￥38,822
￥90,121 total
includes taxes & fees
Oct 5 - Oct 6
Gunstock Chalet - 4BR, Skiing, Concerts, Hiking, & Fall Foliage
A hotel with a swimming pool, solar panels, and a parking lot.

18. Cedar Lodge Condo w/ Loft and private balcony

Cedar Lodge Condo w/ Loft and private balcony
Weirs Beach
10.0 out of 10, Exceptional, (1 review)
"Had an incredible stay for a Father/Son overnight trip to Laconia. The property was clean, incredibly safe, quiet and relaxing, the amenities were very nice and perfect for a vacation of any length. Perfect for family trips, couples getaways, solo adventures and friend getaways. This property is close to anything you want to do in that area. Has a nice pool, basketball, firepit, BBQ spots, places to relax and enjoy your drink or coffee to watch the sunset over the lake or sit under the starry...
United States
Steven F.
The price is ￥19,915
￥41,788 total
includes taxes & fees
Nov 1 - Nov 2
Cedar Lodge Condo w/ Loft and private balcony
A beach with sand, trees, and a boat in the background.

19. 5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!

5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!
Gilford
9.8 out of 10, Exceptional, (25 reviews)
"Was a great place to stay. Had a great time "
United States
Ryan C.
The price is ￥60,650
￥130,859 total
includes taxes & fees
Oct 4 - Oct 5
5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!
A two-story house with a white front porch, a staircase, and a garage.

20. Caretakers -Split level Pet Friendly $50 Fee

Caretakers -Split level Pet Friendly $50 Fee
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"I would stay there again. The caretakers place was just adorable. My stay was very relaxing and the place offered so many activities for children and adults. "
United States
Judith
The price is ￥22,481
￥27,980 total
includes taxes & fees
Oct 30 - Oct 31
Caretakers -Split level Pet Friendly $50 Fee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Little Bear Island Hotel Reviews

Lake Wentworth Inn

Lake Wentworth Inn

8/10 Good
"Room was very clean. Recently totally remodeled not just a paint job. No breakfast. I had some trouble operating the AC but I think it was me. Kinda pricey for what it is and the time of year."
Eugene 1-night trip
Posted 8 hours ago
Lake Wentworth Inn

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