Bear Island Vacation Rentals from $143: Search Short-Term Rentals

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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

Ashland

Mehsan

$132 nightly

Nov 30 - Dec 1

Total with taxes and fees

A hotel with a swimming pool, solar panels, and a parking lot.

2. Cedar Lodge Room 2 Queen Beds & Private Balcony

Weirs Beach

$212 nightly

Nov 15 - Nov 16

Total with taxes and fees

3. Cedar Lodge Condo w/ Loft and private balcony

Weirs Beach

"Had an incredible stay for a Father/Son overnight trip to Laconia. The property was clean, incredibly safe, quiet and relaxing, the amenities were very nice and perfect for a vacation of any length. Perfect for family trips, couples getaways, solo adventures and friend getaways. This property is close to anything you want to do in that area. Has a nice pool, basketball, firepit, BBQ spots, places to relax and enjoy your drink or coffee to watch the sunset over the lake or sit under the starry...

Steven F.

$210 nightly

Nov 15 - Nov 16

Total with taxes and fees

A house with a porch, surrounded by a garden with pink and yellow flowers.

4. Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath

Wolfeboro

Jeanine L.

$156 nightly

Nov 15 - Nov 16

Total with taxes and fees

A waterfall feature with a white fence, surrounded by greenery and a building with large windows.

5. Lakes Region Escape | Private Balcony Near Weirs Beach

Weirs Beach

Adam C.

$189 nightly

Nov 16 - Nov 17

Total with taxes and fees

A beach with boats, a sandy shore, and a clear sky.

6. Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi

Weirs Beach

Darren

$350 nightly

Nov 23 - Nov 24

Total with taxes and fees

7. Cedar Lodge Room-Private Balcony Close to Weirs!

Weirs Beach

Deborah J.

An aerial view of a coastal residential area with multiple houses, a beach, and a body of water.

8. 1 Bedroom Lake Winnipesaukee Condo

Gilford

Radu

$240 nightly

Nov 15 - Nov 16

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and greenery.

9. Weirs beach retreat

Weirs Beach

Wayne W.

$248 nightly

Nov 15 - Nov 16

Total with taxes and fees

A kitchen with a marble countertop, stainless steel sink, and a black pendant light.

10. Incredible Lake & Mtn Views - Loft Vibes Getaway!

Tilton

"The location of this was perfect for us. We went to 2 nights of concerts at the pavilion and the drive was very easy. The location to food and activities was also great! The place was exactly as pictured, very clean, and perfect for our needs. The host was phenomenal, communicative, and even helped us out when we arrived with a flat tire! We look forward to making this "our spot" when we come up for concerts in the future!"

Melissa S.

$243 nightly

Nov 15 - Nov 16

Total with taxes and fees

11. 2 Bedroom Cedar Lodge Condo w/ Loft & private balcony

Weirs Beach

$254 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with picnic tables and lounge chairs, a stone wall, and a view of the lake and distant mountains.

12. Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Gilford

Estuardo

$238 nightly

Dec 1 - Dec 2

Total with taxes and fees

A cozy lounge area with stone walls, wicker furniture, and a self-storage sign.

13. Cozy Studio w/king bed, close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

Laconia

Daniel

$302 nightly

Nov 19 - Nov 20

Total with taxes and fees

A room with a wooden staircase, a sofa with a 'together' pillow, a small table, and a lamp.

14. 10 Min Walk to Lake w/Private HOT TUB & patio!

Laconia

Susan B.

$260 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a large bed, a dining table, and chairs, a chandelier, and a window with curtains.

15. Cupola Suite: Steam Shower, Hot Tub & Fire Pit, Walk the Rail Trail to Wolfeboro

Wolfeboro

$225 nightly

Dec 7 - Dec 8

Total with taxes and fees

A garden with a white pergola, red chairs, and pink flowers.

16. Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

Wolfeboro

Anonymous traveler

$160 nightly

Nov 15 - Nov 16

Total with taxes and fees

17. Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available

Wolfeboro

"No way does this deserve a 10/10 rating. It’s fairly terrible and not deserving such a favorable rating. The pluses - great location, right on the lake. Adirondacks at sunset was heavenly. Super convenient. Wolfeboro is very cute. The shower has been nicely redone. The in-unit washer/dryer worked well and was very convenient. But the negatives are many. Lots of disrepair and terrible attention to detail. We got a spongy soft double bed. The listing says Queen bed. It’s not. We had badly stained...

Brian L.

$256 nightly

Nov 15 - Nov 16

Total with taxes and fees