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 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 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
$147 nightly
The price is $160
Oct 25 - Oct 26
Total with taxes and fees
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.
$218 nightly
The price is $229
Oct 28 - Oct 29
Total with taxes and fees
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
$255 nightly
The price is $277
Nov 2 - Nov 3
Total with taxes and fees
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.
$173 nightly
The price is $188
Oct 5 - Oct 6
Total with taxes and fees
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.
$203 nightly
The price is $220
Oct 15 - Oct 16
Total with taxes and fees
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
$320 nightly
The price is $347
Oct 19 - Oct 20
Total with taxes and fees
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.
$262 nightly
The price is $284
Oct 12 - Oct 13
Total with taxes and fees
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
$422 nightly
The price is $458
Oct 13 - Oct 14
Total with taxes and fees
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 traveler
$163 nightly
The price is $176
Oct 6 - Oct 7
Total with taxes and fees
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
$153 nightly
The price is $166
Oct 5 - Oct 6
Total with taxes and fees
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
$216 nightly
The price is $235
Oct 29 - Oct 30
Total with taxes and fees
Newly Renovated Cottage 3 on Main Street Alton Bay!
A coastal town with a marina, a large cruise ship docked, and a beach.

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.
$212 nightly
The price is $231
Oct 5 - Oct 6
Total with taxes and fees
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
$286 nightly
The price is $303
Oct 13 - Oct 14
Total with taxes and fees
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
$163 nightly
The price is $176
Nov 1 - Nov 2
Total with taxes and fees
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.
$328 nightly
The price is $357
Nov 1 - Nov 2
Total with taxes and fees
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
$233 nightly
The price is $245
Oct 5 - Oct 6
Total with taxes and fees
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
$344 nightly
The price is $373
Oct 6 - Oct 7
Total with taxes and fees
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
$207 nightly
The price is $217
Oct 28 - Oct 29
Total with taxes and fees
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.
$389 nightly
The price is $422
Nov 2 - Nov 3
Total with taxes and fees
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

Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

10/10 Excellent
"Staff was very helpful and friendly, the breeze restaurant was awesome on food and drinks, and reasonably priced for high end place.not far from there. No public beach nearby, have to go north for access. Got a room with fireplace was awesome, especially for cheap price."
Joseph 1-night trip
Posted 14 hours ago
Fireside Inn & Suites Gilford

Find out more about Bear Island

Everything you need to know about Bear Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bear Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bear Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bear Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bear Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bear Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $160 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bear Island rentals

At Expedia, we put the best Bear Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bear Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bear Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bear Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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