Vacation rentals in Winter Harbor

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Top-rated vacation rentals in Winter Harbor

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Tamworth

4.9 out of 5 average rating, 433 reviews

Luxurious Mountainside Cabin! Fantastic Views!

Mountainside Cabin with Sweeping Mountain Views! A great escape with total privacy. Wood Fired Sauna on the premises! Relax by the Giant Fire Pit overlooking the Mountains! Head up to North Conway or to Mt. Washington or go South to the Lakes Region. Then escape the traffic and retreat to the quiet of your Mountainside Cabin. We provide everything you will need for your stay, and I mean everything, just bring a sense of adventure! Pets Yes! *Pet Fee Applies! *Additional Fee for Sauna

Jun 9 – 16

$136 per night
Guest favorite

Cottage in Alton

4.87 out of 5 average rating, 156 reviews

1 Bedroom Cottage w/Lake Winnipesaukee View/Access

Quaint 1 bedroom cottage w/views of Lake Winnipesaukee has AC w/beach toys & available year-round. Our deck is literally on Lake Winnipesaukee and a 3 minute walk from the cottage. Here you will be able to enjoy gorgeous views, watch & participate in lake activities such as swimming off our dock or jumping off the diving board. The public beach is steps away, along with restaurants, ice cream, water sport rentals, mini-golf & entertainment. Perfect for couples or small family & is pet friendly.

Feb 3 – 10

$116 per night
Guest favorite

Home in Lebanon

4.96 out of 5 average rating, 158 reviews

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Oct 22 – 29

$105 per night

Popular amenities for Winter Harbor vacation rentals

Other great vacation rentals in Winter Harbor

Guest favorite

Guest suite in Meredith

4.86 out of 5 average rating, 102 reviews

Meredith Manor, Suite in Town

Apr 23 – 30

$91 per night
Guest favorite

Guest suite in Wolfeboro

4.82 out of 5 average rating, 94 reviews

Downtown, Cozy, Cute, and Convenient!

Oct 15 – 22

$92 per night
Guest favorite

Cottage in Wolfeboro

4.95 out of 5 average rating, 81 reviews

Cozy Cottage by Lake Winnie

Apr 8 – 15

$234 per night
Guest favorite

Home in Wolfeboro

4.92 out of 5 average rating, 52 reviews

Lakefront Winnipesaukee Home

Jan 22 – 29

$900 per night
Guest favorite

Apartment in Wakefield

5.0 out of 5 average rating, 53 reviews

Clean, quaint studio apartment on small farm

Nov 30 – Dec 7

$85 per night
Superhost

Cabin in Tuftonboro

5.0 out of 5 average rating, 9 reviews

Bear Paw

May 7 – 14

$267 per night
Superhost

Home in Wolfeboro

4.89 out of 5 average rating, 19 reviews

The wolf den in Wolfeboro

Nov 27 – Dec 4

$338 per night
Guest favorite

Apartment in Alton

4.95 out of 5 average rating, 63 reviews

Pretty & Peaceful….close to Lake Winni!

Mar 19 – 26

$106 per night
Guest favorite

Cottage in Wolfeboro

4.98 out of 5 average rating, 62 reviews

Quaint Wolfeboro Lake Winnipesaukee Lakefront Home

Dec 19 – 26

$445 per night
Guest favorite

Apartment in Wolfeboro

4.96 out of 5 average rating, 26 reviews

2-bedroom unit surrounded by recreation and nature

Aug 30 – Sep 6

$162 per night
Guest favorite

Guesthouse in Wolfeboro

5.0 out of 5 average rating, 42 reviews

5 Star Lake Cottage -Wolfeboro

Dec 22 – 29

$369 per night
Guest favorite

Home in Gilford

5.0 out of 5 average rating, 45 reviews

Quiet 2 bedroom, One Bathroom with beautiful views

Feb 25 – Mar 4

$204 per night

Destinations to explore