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

Bear Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for 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, (280 reviews)
"Great place, value for money"
Canada
Abhishek
The price is ￥17,287
￥18,756 total
includes taxes & fees
Nov 1 - Nov 2
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, (22 reviews)
"The room was nice. Great view of the lake."
United States
Brandy a.
The price is ￥15,847
￥36,608 total
includes taxes & fees
Oct 26 - Oct 27
Cute Cedar Lodge Studio with Balcony & Lake Views!
A garden with a white pergola, red chairs, and pink flowers.

3. 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 ￥22,417
￥27,758 total
includes taxes & fees
Oct 26 - Oct 27
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A beach with picnic tables and lounge chairs, a stone wall, and a view of the lake and distant mountains.

4. 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 ￥21,575
￥43,033 total
includes taxes & fees
Nov 4 - Nov 5
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
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 ￥14,420
￥35,441 total
includes taxes & fees
Oct 22 - Oct 23
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, (33 reviews)
"Easy process and great location"
United States
Daniel
The price is ￥23,509
￥53,335 total
includes taxes & fees
Oct 15 - Oct 16
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 ￥16,623
￥45,003 total
includes taxes & fees
Oct 14 - Oct 15
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
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
9.6 out of 10, Exceptional, (14 reviews)
"Great place "
United States
Anonymous traveler
The price is ￥22,227
￥27,551 total
includes taxes & fees
Oct 15 - Oct 16
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A laundry room with a table, a refrigerator, and multiple washing machines.

10. Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach

Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach
Weirs Beach
10.0 out of 10, Exceptional, (3 reviews)
"Good location with clean and comfortable beds. Thx!"
United States
Phil C.
The price is ￥16,816
￥35,115 total
includes taxes & fees
Nov 1 - Nov 2
Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach
A two-story house with a white front porch, a staircase, and a garage.

11. 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 ￥21,087
￥26,314 total
includes taxes & fees
Oct 22 - Oct 23
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.

12. 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 ￥18,402
￥37,331 total
includes taxes & fees
Oct 27 - Oct 28
Newly Renovated Cottage 3 on Main Street Alton Bay!
A large building with multiple sections, surrounded by snow-covered ground and trees, with a lake and mountains in the background.

13. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is ￥19,370
￥41,521 total
includes taxes & fees
Nov 9 - Nov 10
Cedar Lodge Room 2 Queen Beds & Private Balcony
A large, modern building with multiple floors and a flat roof, surrounded by a snowy landscape and a body of water in the background.

14. 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 ￥14,105
￥34,536 total
includes taxes & fees
Oct 26 - Oct 27
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
A cozy living room with a stone fireplace, wooden walls, and large windows offering a view of the outdoors.

15. Mountain Cabin with long range views, privacy, and more.

Mountain Cabin with long range views, privacy, and more.
Campton
9.4 out of 10, Exceptional, (13 reviews)
"Great location, beautiful views, and everything we could want, from amenities to the communication."
United States
Robert G.
The price is ￥13,132
￥45,166 total
includes taxes & fees
Nov 2 - Nov 3
Mountain Cabin with long range views, privacy, and more.
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 ￥18,364
￥56,571 total
includes taxes & fees
Oct 26 - Oct 27
Newly Renovated Cottage 4 in Alton Bay, NH
A living room with a stone fireplace, a ceiling fan, and a large window.

17. 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 ￥20,788
￥71,094 total
includes taxes & fees
Nov 2 - Nov 3
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
A kitchen with a granite countertop, white cabinets, a built-in stove, and a hanging light fixture.

18. 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 ￥30,166
￥59,563 total
includes taxes & fees
Nov 9 - Nov 10
Lake Winni Waterfront Condo
A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dining table with a placemat and a bowl.

19. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
Center Tuftonboro
10.0 out of 10, Exceptional, (16 reviews)
"Property was just as pictured. Great location near the pond. Home had everything I could have needed, including a few snacks. Bit of a snafu on check-in but host communication was quick and pleasant!"
United States
Diane S.
The price is ￥26,121
￥74,546 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Tuftonboro Escape: Steps to Private Beaches!
A lakeside view with a boat on the water, a table with chairs, and a tent.

20. 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 ￥24,906
￥50,261 total
includes taxes & fees
Oct 14 - Oct 15
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
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

Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

8/10 Good
"Nice stay. Good amenities. Nice staff. Just don’t dine at Hectors around the corner. It sucks."
Julian 1-night trip
Posted 10 hours ago
Best Western Plus Landmark Inn

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