Vacation rentals in Winter Harbor

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Top-rated vacation rentals in Winter Harbor

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Top guest favorite

A spacious outdoor patio is presented, featuring a rectangular fire pit surrounded by comfortable seating. The area is bordered by a natural stone wall, and the landscape includes trees and open views of the surroundings under a colorful sky.

Farm stay in Alton

4.98 out of 5 average rating, 241 reviews

Mountain View - Modern & Beautiful

Kick back and relax in this stylish apartment space, with its own entrance around the back of the home! Modern construction w/ a king bed, large outdoor patio space w/ mountain views. 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 a private space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

Top guest favorite

The interior features a wooden ceiling with exposed beams, where decorative items are mounted on the walls. Two deer heads are positioned above a pair of windows, allowing natural light to illuminate the space. A modern lamp hangs centrally, contributing to the rustic decor.

Place to stay in Moultonborough

4.96 out of 5 average rating, 109 reviews

Secluded cabin with off grid capabilities

If your looking for a place to get away from it all and just relax this is the place for you! Located in the Northern Lakes Region on a major wildlife corridor this rustic hunting cabin has off the grid accessories including battery powered lights, outside cold shower with an outside sink and a outhouse. There are walking trails and abundant wildlife from deer, bear, moose and coyotes all of which you may encounter. The peepers will lull you to sleep at night. Pristine beach and hiking close by.

Guest favorite

A brick wall is complemented by a decorative wreath of greenery and lavender. Shelving on the adjacent wall contains woven baskets and rolled towels, adding a functional element to the entryway. A white door provides access to the space.

Guest suite in Wolfeboro

4.86 out of 5 average rating, 146 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

Two weathered wooden chairs are positioned around a fire pit made of natural stones, situated on a grassy area surrounded by lush green trees. The serene setting offers a peaceful space for relaxation.

Apartment in Alton

4.98 out of 5 average rating, 153 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 modern, gray-sided building showcases a welcoming front entrance with a dark door. Two windows on either side allow natural light to enter. Flower beds with colorful plants provide a vibrant contrast, and a small stone step leads up to the entrance.

Apartment in Wolfeboro

4.89 out of 5 average rating, 19 reviews

Peaceful getaway with King Bed near Town

Welcome to the perfect Wolfeboro Getaway! King size memory foam mattress for a rejuvenating nights sleep. You will love the peace and quiet of this location with easy walkable access to everything in downtown Wolfeboro, Back Bay, and the waterfront. For nature lovers, there's hiking trails right at the end of the street, just take a left out the front door. Please note: There is a kitchenette with sink, refrigerator, coffee maker, toaster oven, and plug in cook top but no actual stove.

Guest favorite

Cottage in Wolfeboro

4.95 out of 5 average rating, 110 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 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, 204 reviews

Romantic A-Frame cabin in the woods

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 winter scene showcases charming homes nestled among snow-covered trees. The landscape is blanketed in white, with the blue and grey facades of the houses contrasting the snowy surroundings. The tranquil atmosphere is complemented by the stillness of the winter day.

Condo in Wolfeboro

4.96 out of 5 average rating, 139 reviews

Downtown Wolfeboro condo on Winnipesaukee w/Dock!

It's one thing to be right downtown in beautiful Wolfeboro, but add being right on the water w/your own porch, as you look over Wolfeboro Bay. Always something beautiful in front of you. This was my personal unit for a couple of years. It's fully equipped with a brand new bathroom lrg. tile shower, full kitchen, 55" UHD TV, Hi-Speed Internet, new Split System AC is comfy & quiet & a lrg. sectional couch that'll sleep-2 very comfortably. Lake living at its finest.

Top guest favorite

A modern cabin with a black exterior is surrounded by a serene winter landscape, featuring snow-covered trees and a blanket of snow on the ground. A wooden deck extends from the cabin, blending with the natural surroundings in this peaceful winter setting.

Home in Bridgton

5 out of 5 average rating, 104 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Guest favorite

An aerial view captures a serene lakeside setting, featuring a sandy beach lined with lounge chairs. Several boats are docked along the shore, while trees and buildings provide a natural backdrop, creating an inviting space for outdoor relaxation and activities.

Condo in Gilford

4.92 out of 5 average rating, 202 reviews

Lake or Ski Condo, close to Gunstock and the Lake

Location and Amenities! 10 min from Gunstock, couple hundred yards from the Lake, 50 yards from Gilford concert stage and the back entrance. Access to Barefoot Beach, Lake Winnipesaukee, outdoor pool, tennis courts, grill high speed WiFi and more. 1 Bedroom studio and a pull out couch, sleeps 4 comfortably. Large bathroom and shower. Ski 10 min away or ice fish 150 yards away. Laconia Bike week only Minutes away! 1 Free parking spot.

Top guest favorite

The interior of the barn features exposed wooden beams and spacious areas. A leather sofa is positioned in the foreground, with a view of a bar and kitchen area in the background. Large windows allow natural light to fill the open space, complementing the rustic charm.

Guesthouse in Wolfeboro

4.98 out of 5 average rating, 198 reviews

A charming loft Barn that sleeps 5.

Our 3000 sq ft renovated, rustic loft barn is located on 70 acres, very private, yet 2.5 miles from downtown Wolfeboro. Our barn sleeps 5, has full kitchen, bar, pool table, 65 inch TV and bath with shower. The barn has 1 queen & 4 single beds in the loft. A perfect place to hang out with a few friends. Minimum age of primary renter 25. MAX 5 guests staying, please do not book if you have more. No parties.

Top guest favorite

The kitchen area features a modern design with a central island, complemented by black stools. Open shelving displays glassware above a contemporary range. A stainless steel refrigerator stands nearby, while wooden beams and large windows enhance the spacious, airy atmosphere.

Barn in Wolfeboro

4.95 out of 5 average rating, 108 reviews

The Barn at Crescent Lake

Welcome to Wolfeboro, New Hampshire! Our barn is located just outside of downtown Wolfeboro, filled with multiple shops and eateries! Our home is on Crescent Lake, with private beach access and a dock with a boat slips if needed. The home is located off of Wolfeboro's Cotton Valley Rail tail, a peaceful walking path that begins in downtown and passes through several towns!