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Holiday rentals in Winter Harbor

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Popular amenities for Winter Harbor holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Homes with more space

Top guest favourite
A side view of a charming green cottage is presented, featuring white trim and multiple windows that allow natural light inside. The surrounding area is lush with greenery, and a well-maintained path leads up to the entrance.
Bungalow in Wolfeboro
4.95 out of 5 average rating, 94 reviews

2 Bedroom Guest Cottage. Close to town

Guest favourite
A home surrounded by lush greenery features a gravel area with a fire pit and several chairs arranged around it. The exterior displays large windows, and a screened porch extends from the home, providing views of the tranquil landscape.
Home in Wolfeboro
4.87 out of 5 average rating, 31 reviews

Lake House with Screen Porch

Guest favourite
A log cabin surrounded by trees is situated near the shoreline of the Ossipee River. A wooden deck extends from the cabin, and a red tandem kayak is positioned on a small dock, creating an inviting space for outdoor activities.
Cabin in Parsonsfield
4.95 out of 5 average rating, 253 reviews

Riverfront cabin between Portland & White Mtns.

Top guest favourite
A cozy living area displays a light sofa and an accent chair, both complemented by soft throw pillows. A coffee table sits centrally beneath a ceiling fan. Light streams in through the windows, highlighting the warm wood tones of the space and the adjoining dining area.
Home in Wolfeboro
4.97 out of 5 average rating, 32 reviews

Quaint Wolfeboro NH Home.

Destinations to explore