Vacation rentals in Winter Harbor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winter Harbor

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

A cabin with a spacious deck overlooks a natural setting. The structure features large windows and a bright red umbrella set over a wooden table. Surrounding green trees and shrubs create a serene environment, while a canoe rests nearby on the ground.

Home in Wolfeboro

4.99 out of 5 average rating, 133 reviews

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Top guest favorite

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

5 out of 5 average rating, 225 reviews

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Top guest favorite

A wooden deck features several black Adirondack chairs positioned to take in the surrounding landscape. Lush green fields and trees are visible in the distance, under a clear sky with soft clouds, creating an inviting space for outdoor relaxation.

Guest suite in Alton

4.99 out of 5 average rating, 421 reviews

Treehouse @ The Vineyard - Beautiful inside & out

Kick back and relax in this calm, stylish apartment space. This space is an open concept with a king size bed. Lots of windows bring in natural light, cathedral ceiling and amazing view! A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have your own space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 20 min to Gunstock and 25 min to Bank of Pavilion

Superhost

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

4.9 out of 5 average rating, 532 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Guest favorite

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

4.92 out of 5 average rating, 25 reviews

Lake House with Screen Porch

Relax with the whole family at this peaceful home on lake Winnipesaukee. Home was fully renovated in 2024 and has a screen porch with water views, and a large yard with fire pit. Located on a private road in a quiet neighborhood. Just a minute walk to the water. Community areas include a sandy beach, swim area and raft, docks, a boathouse with ping pong & screen porch overlooking the water. Home is located just 2 miles from downtown Wolfeboro with many events, shops & great restaurants.

Guest favorite

A bedroom features a spacious bed dressed in neutral linens, complemented by a decorative pillow. A nightstand holds a lamp with a soft light. Natural light filters through vertical blinds, enhancing the serene atmosphere. A framed black-and-white photograph reflects a peaceful lake scene.

Guest suite in Wolfeboro

4.87 out of 5 average rating, 163 reviews

Downtown, Cozy, Cute, and Convenient!

Walk just one block to the heart of downtown Wolfeboro, the "Oldest Summer Resort in America". Dine, shop, visit art galleries, or just relax in the park overlooking the docks on Wolfeboro Bay. Take the Mt Washington Ferry for a Lake Winnipesaukee ride or Molly the Trolley hop on/off tour. The rail trail is close by and a playground is just steps away for the little ones. Also, Wolfeboro’s best Mexican restaurant, coffee shops, Hunter’s grocery and Walgreens are all just a short walk away!

Top guest favorite

A charming entrance showcases cream-colored siding and a staircase leading up to the front door. Flanking the steps, lush greenery frames the pathway. A wooden bench with a pillow sits beside the entrance, with a small American flag hanging nearby.

Apartment in Alton

4.98 out of 5 average rating, 174 reviews

Pretty & Peaceful….close to Lake Winni!

Welcome to your Alton Bay retreat! Come relax & make lasting memories. Very clean, well stocked full kitchen & bath. Across the street is 200 acres of picturesque hiking trails & fishing. Turn left at the end of driveway and enjoy a scenic walk along Winni. Quiet location but close enough to Lake Winnipesaukee, Mt Major, Wolfeboro, Bank of Pavillion, boat launches, & docks, beaches, restaurants, shopping, sking, snowmobiling, boat rides, scuba diving, biking, kayaking, leaf peeping!

Guest favorite

A private dock extends over the calm waters, featuring two red Adirondack chairs facing the serene lake. An American flag waves gently on a pole, surrounded by vibrant autumn foliage reflected in the water.

Cabin in Tuftonboro

4.95 out of 5 average rating, 20 reviews

Bear Paw

The Pow Wow Lodge property has been a family run business colony since 1963. These vintage cottages offers guests the perfect vacation spot to relax, unwind and enjoy all the area has to offer. Experience the beauty, nature and quietness of this pristine lake with your own private dock along with breathtaking mountain views. Spend your time swimming, boating, fishing, paddle boarding with golf, tennis, shopping, sightseeing, antiquing, hiking and dining are all conveniently close by.

Guest favorite

The sandy beach area features several white adirondack chairs arranged for relaxation. Gentle waves lap at the shoreline, where boats are anchored in the distance. A staircase leads up from the beach to a grassy area, surrounded by trees, under a clear sky.

Cottage in Wolfeboro

4.96 out of 5 average rating, 117 reviews

Lake Winnie Cozy Cottage Getaway

Welcome to Lake a Dream… Here is your chance for a fun filled family vaca on Lake Winnie in the summer or a cozy couples getaway in the winter! With just a quick 3 minute walk you can enjoy some sunshine & sand on the beach! Or a 5 minute drive into downtown Wolfeboro to experience it’s charm; waterfront dining, ice cream, shops, cafés & more! For winter stays, cozy up by the fireplace with a cup of hot cocoa & some fun family games! The cottage is not far from Gunstock & Kingpine.

Top guest favorite

A dining area features a rustic wooden table surrounded by two woven chairs. Light from a pendant lamp highlights floral artwork on the wall. Beyond, a cozy living space is visible, furnished with a pink sofa and a green table, framed by a large window.

Guesthouse in Wolfeboro

5 out of 5 average rating, 41 reviews

Sugar Hill Cottage Suite

Come and enjoy a relaxing stay at Sugar Hill Cottage suite and experience New England seasons and all they have to offer, 5 minutes from Lake Winnipesaukee and downtown Wolfeboro, 3 minutes to Abenaki Ski Area and 30 minutes from Gunstock Ski Resort. Nestled amongst Sugar Maples on 13 acres attached to the host's home with separate private entrance. You are sure to enjoy a cozy retreat. Apartment boasts King size bed, custom kitchen with washer/dryer, full bath and fast internet.

Guest favorite

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

4.96 out of 5 average rating, 28 reviews

Quaint Wolfeboro NH Home.

Quaint Wolfeboro NH Short-Term Rental - Centrally Located Welcome to our charming short-term rental in Wolfeboro, NH! Located just 5 minutes from downtown Wolfeboro, our cozy Cape home offers a perfect getaway for those looking to explore the beauty and amenities of this historic lakeside town. With its convenient location, you'll have easy access to great restaurants, shopping, walking trails, a public golf course, museums, Molly the Trolly, beaches, and lakeside activities.

Guest favorite

A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.

Cottage in Middleton

4.96 out of 5 average rating, 195 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!