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, (282 reviews)
"Great place, value for money"
Canada
Abhishek
$148 nightly
The price is $161
Nov 1 - Nov 2
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, (22 reviews)
"The room was nice. Great view of the lake."
United States
Brandy a.
$220 nightly
The price is $231
Oct 26 - Oct 27
Total with taxes and fees
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
$163 nightly
The price is $176
Oct 27 - Oct 28
Total with taxes and fees
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
$253 nightly
The price is $275
Nov 2 - Nov 3
Total with taxes and fees
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.
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, (34 reviews)
"Easy process and great location"
United States
Daniel
$281 nightly
The price is $305
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)
$260 nightly
The price is $282
Oct 18 - Oct 19
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
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
$160 nightly
The price is $174
Oct 18 - Oct 19
Total with taxes and fees
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.
$191 nightly
The price is $207
Nov 2 - Nov 3
Total with taxes and fees
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
$153 nightly
The price is $166
Oct 22 - Oct 23
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.

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
$223 nightly
The price is $243
Oct 29 - Oct 30
Total with taxes and fees
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
$233 nightly
The price is $245
Oct 17 - Oct 18
Total with taxes and fees
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
$208 nightly
The price is $218
Oct 26 - Oct 27
Total with taxes and fees
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.
$263 nightly
The price is $285
Nov 2 - Nov 3
Total with taxes and fees
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.
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.
$413 nightly
The price is $448
Nov 3 - Nov 4
Total with taxes and fees
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
$359 nightly
The price is $378
Oct 19 - Oct 20
Total with taxes and fees
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.
$437 nightly
The price is $474
Oct 18 - Oct 19
Total with taxes and fees
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.
$316 nightly
The price is $343
Oct 21 - Oct 22
Total with taxes and fees
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

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

10/10 Excellent
"Everything exceeded our expectations. The check-in process was seamless, the amenities were top-notch, and the location was ideal. Truly a 5-star experience!"
Madhan 2-night trip
Posted 13 hours ago
Cold Spring Plymouth Resort

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 $161 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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