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, (271 reviews)
"Had a great weekend stay."
United States
Armand
The price is HK$1,038
HK$1,127 total
includes taxes & fees
27 Oct - 28 Oct
Cold Spring Plymouth Resort
A spacious kitchen with wooden beams, a large dining table, and a fireplace.

2. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (2 reviews)
"We’ll kept "
United States
Denise
The price is HK$1,663
HK$3,627 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A modern kitchen with white cabinets, a built-in microwave, and a dishwasher. There are two bar stools near the kitchen counter.

3. 9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
8.0 out of 10, Very good, (2 reviews)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is HK$1,797
HK$2,830 total
includes taxes & fees
4 Oct - 5 Oct
9 Lake Street
A wide sandy beach with a calm lake and dense green trees in the background.

4. Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
3.0 star property
Locke Lake Colony
Quiet New Hampshire Getaway w/ Game Room!
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

Lake Wentworth Inn

Lake Wentworth Inn

8/10 Good
"Room was very clean. Recently totally remodeled not just a paint job. No breakfast. I had some trouble operating the AC but I think it was me. Kinda pricey for what it is and the time of year."
Eugene 1-night trip
Posted 4 hours ago
Lake Wentworth Inn

Find out more about Bear Island

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