A lakeside town with autumn-colored trees, a church, and a large white building with a green roof.

Bear Island Holiday Rentals

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Check prices for these dates

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

Our top choices for Bear Island holiday 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, (272 reviews)
"Had a great weekend stay."
United States
Armand
The price is HK$1,039
HK$1,127 total
includes taxes & fees
25 Oct - 26 Oct
Cold Spring Plymouth Resort
A narrow hallway leading to a bathroom with a sink and mirror. A bed is visible in the adjacent room.

2. Cute Cedar Lodge Studio with Balcony & Lake Views!

Cute Cedar Lodge Studio with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (21 reviews)
"The room was nice. Great view of the lake."
United States
Brandy a.
The price is HK$768
HK$1,796 total
includes taxes & fees
28 Oct - 29 Oct
Cute Cedar Lodge Studio with Balcony & Lake Views!
A beach with picnic tables and lounge chairs, a stone wall, and a view of the lake and distant mountains.

3. 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 HK$1,091
HK$2,171 total
includes taxes & fees
2 Nov - 3 Nov
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
A serene lakeside view at sunset with a silhouette of trees and a calm water surface.

4. 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 HK$1,196
HK$1,476 total
includes taxes & fees
5 Oct - 6 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A lakeside property with a dock, boats, and a large building surrounded by trees.

5. Gilford Perfect Getaway Pool, WIFI & Free Parking

Gilford Perfect Getaway Pool, WIFI & Free Parking
Laconia
8.4 out of 10, Very good, (7 reviews)
"Very nice place, easily located near everything. Would definitely stay here again."
United States
Katherine B.
The price is HK$713
HK$1,762 total
includes taxes & fees
11 Oct - 12 Oct
Gilford Perfect Getaway Pool, WIFI & Free Parking
A cozy lounge area with stone walls, wicker furniture, and a self-storage sign.

6. 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 HK$1,201
HK$2,725 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and greenery.

7. Weirs beach retreat

Weirs beach retreat
Weirs Beach
9.8 out of 10, Exceptional, (8 reviews)
"Just a minutes drive to the waterfront and shops. Great location "
United States
Wayne W.
The price is HK$824
HK$2,231 total
includes taxes & fees
12 Oct - 13 Oct
Weirs beach retreat
A cozy living room with a brown leather sofa, a wooden coffee table, and a fish-themed wall decoration.

8. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
The price is HK$910
HK$3,592 total
includes taxes & fees
13 Oct - 14 Oct
Lake Winnipesaukee Home for Fall & Winter Fun
A garden with a white pergola, red chairs, and pink flowers.

9. Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.4 out of 10, Exceptional, (13 reviews)
"Great place "
United States
Anonymous traveller
The price is HK$1,111
HK$1,385 total
includes taxes & fees
6 Oct - 7 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A two-story house with a white front porch, a staircase, and a garage.

10. 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 HK$1,045
HK$1,304 total
includes taxes & fees
6 Oct - 7 Oct
Caretakers -Split level Pet Friendly $50 Fee
A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

11. Newly Renovated Cottage 3 on Main Street Alton Bay!

Newly Renovated Cottage 3 on Main Street Alton Bay!
Alton
9.6 out of 10, Exceptional, (7 reviews)
"Staff was very freindly"
United States
David
The price is HK$910
HK$1,847 total
includes taxes & fees
29 Oct - 30 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!
A golf course with a water body in the background, surrounded by trees and a parking area.

12. Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
Alton
8.8 out of 10, Excellent, (14 reviews)
"Nicely kept enjoyable stay"
United States
Shirley G.
The price is HK$863
HK$1,812 total
includes taxes & fees
5 Oct - 6 Oct
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
A large building with multiple sections, surrounded by snow-covered ground and trees, overlooking a large body of water.

13. Cedar Lodge condo with mountain & lake Winnipesauke views!

Cedar Lodge condo with mountain & lake Winnipesauke views!
Weirs Beach
9.2 out of 10, Wonderful, (58 reviews)
"The room was adequate. Clean but not superclean!"
United States
Walter
The price is HK$1,226
HK$2,380 total
includes taxes & fees
13 Oct - 14 Oct
Cedar Lodge condo with mountain & lake Winnipesauke views!
A deck with two wicker chairs, a table, and a view of a lake.

14. Gorgeous Waterfront Condo with Lake Access & Views

Gorgeous Waterfront Condo with Lake Access & Views
Tilton
9.8 out of 10, Exceptional, (51 reviews)
"Lake View is beautiful and unobstructed inside very clean and inviting keurig and regular coffee maker. Very nice place wish we could’ve stayed longer."
United States
Catherine
Gorgeous Waterfront Condo with Lake Access & Views
A garden with a white pergola, red chairs, and pink flowers.

15. Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (6 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is HK$1,111
HK$1,385 total
includes taxes & fees
2 Nov - 3 Nov
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A cozy room with a wicker sofa, a wooden ladder shelf, and a large wooden-framed window.

16. Newly Renovated Cottage 4 in Alton Bay, NH

Newly Renovated Cottage 4 in Alton Bay, NH
Alton
9.0 out of 10, Wonderful, (4 reviews)
"Communication was amazing, check in was a delightful, the house itself was perfect "
United States
Jennifer S.
The price is HK$910
HK$2,804 total
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated Cottage 4 in Alton Bay, NH
A large building with multiple sections, surrounded by snow-covered ground and trees, with a lake and mountains in the background.

17. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is HK$863
HK$1,925 total
includes taxes & fees
5 Oct - 6 Oct
Cedar Lodge Room 2 Queen Beds & Private Balcony
A bedroom with a bed, bedside tables, a wardrobe, and a kitchen area.

18. Picturesque Studio Lakefront - Dock

Picturesque Studio Lakefront - Dock
Alton
The price is HK$1,295
HK$2,928 total
includes taxes & fees
6 Oct - 7 Oct
Picturesque Studio Lakefront - Dock
A large, modern building with multiple floors and a flat roof, surrounded by a snowy landscape and a body of water in the background.

19. Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (7 reviews)
"Property was very clean, had very comfortable beds and a wonderful view. "
United States
Crystal
The price is HK$691
HK$1,703 total
includes taxes & fees
28 Oct - 29 Oct
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
A living room with a stone fireplace, a ceiling fan, and a large window.

20. Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8

Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
Gilford
10.0 out of 10, Exceptional, (1 review)
"Home was clean Host was easy to communicate with"
United States
Robert L.
The price is HK$918
HK$3,312 total
includes taxes & fees
2 Nov - 3 Nov
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
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 Bear Island Hotel Reviews

Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

10/10 Excellent
"Great place"
Marc 2-night trip
Posted less than an hour ago
Mill Falls Resort Collection at the Lake

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