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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Our top choices for Bear Island holiday rentals

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 NZ$256
includes taxes & fees
25 Oct - 26 Oct
Cold Spring Plymouth Resort

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 NZ$401
includes taxes & fees
28 Oct - 29 Oct
Cute Cedar Lodge Studio with Balcony & Lake Views!

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 NZ$430
includes taxes & fees
19 Oct - 20 Oct
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

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 NZ$334
includes taxes & fees
5 Oct - 6 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard

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 NZ$385
includes taxes & fees
15 Oct - 16 Oct
Gilford Perfect Getaway Pool, WIFI & Free Parking

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 NZ$608
includes taxes & fees
19 Oct - 20 Oct
Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

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 NZ$495
includes taxes & fees
14 Oct - 15 Oct
Weirs beach retreat

8. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
The price is NZ$817
includes taxes & fees
13 Oct - 14 Oct
Lake Winnipesaukee Home for Fall & Winter Fun

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 NZ$313
includes taxes & fees
19 Oct - 20 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

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 NZ$297
includes taxes & fees
5 Oct - 6 Oct
Caretakers -Split level Pet Friendly $50 Fee

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 NZ$410
includes taxes & fees
29 Oct - 30 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!

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 NZ$402
includes taxes & fees
4 Oct - 5 Oct
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

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 NZ$527
includes taxes & fees
4 Oct - 5 Oct
Cedar Lodge condo with mountain & lake Winnipesauke views!

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
The price is NZ$624
includes taxes & fees
4 Oct - 5 Oct
Gorgeous Waterfront Condo with Lake Access & Views

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 NZ$313
includes taxes & fees
1 Nov - 2 Nov
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

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 NZ$633
includes taxes & fees
21 Oct - 22 Oct
Newly Renovated Cottage 4 in Alton Bay, NH

17. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is NZ$436
includes taxes & fees
4 Oct - 5 Oct
Cedar Lodge Room 2 Queen Beds & Private Balcony

18. Picturesque Studio Lakefront - Dock

Picturesque Studio Lakefront - Dock
Alton
The price is NZ$661
includes taxes & fees
13 Oct - 14 Oct
Picturesque Studio Lakefront - Dock

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 NZ$381
includes taxes & fees
28 Oct - 29 Oct
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

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 NZ$788
includes taxes & fees
5 Oct - 6 Oct
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

Find out more about Bear Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Bear Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Bear Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Bear Island. Seeing all the best attractions is bound to make you fall in love with Bear Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Bear Island short-term rentals, that won’t be hard to do.

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