Holiday houses in Winter Harbor

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Top-rated holiday rentals in Winter Harbor

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Guest favourite

Farm stay in Alton

4.99 out of 5 average rating, 309 reviews

Treehouse Penthouse ❤ 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, 25 min to Gunstock and 25 min to Bank of Pavilion

Guest favourite

Apartment in Alton

4.96 out of 5 average rating, 71 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 favourite

Guesthouse in Belmont

4.99 out of 5 average rating, 201 reviews

Charming Pool/Garden Guest House

A little Paradise! Charming pool and guesthouse in country setting, birds and flowers galore. Much to do in the area, or just quiet, settling into some refresh-your-soul time. The guesthouse has all you need to feel at home. Within 15 minutes you'll find Gunstock Recreational Area, Highlands Mtn. Bike Park, Hermit Woods Winery, Funspot bowling and arcades, hiking, fishing, Shaker Village, Lakes Region Casino, NH Speedway, Bank of America Pavillion (concerts) and Tanger Outlet Shopping.

Superhost

Cabin in Tuftonboro

5.0 out of 5 average rating, 10 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 favourite

Apartment in Campton

4.92 out of 5 average rating, 171 reviews

White Mountain is a Special Place

Renovated modern farmhouse studio in the White Mountains. We are the 4th generation in our family’s home. Posts and beams with new kitchen, shiplap, hardwood floors, and large bathroom, and great view overlooking the fields. 36 acres of field, woods, and cut your Christmas Tree here. If lucky you will catch a glimpse of the horses in the field. Close to hiking, skiing, and lakes. Waterville Valley 9 miles, Loon Mtn. 15 miles. Owls Nest Golf Couse. Private entry /private studio.

Guest favourite

Cottage in Wolfeboro

4.95 out of 5 average rating, 82 reviews

Cozy Cottage by Lake Winnie

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.

Guest favourite

Guesthouse in Wolfeboro

4.98 out of 5 average rating, 178 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 double & 4 single beds, one set of single beds can be converted into a king upon request prior to stay. 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.

Guest favourite

Condo in Wolfeboro

4.97 out of 5 average rating, 110 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.

Guest favourite

Cottage in Middleton

4.96 out of 5 average rating, 142 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!

Guest favourite

Condo in Gilford

4.9 out of 5 average rating, 134 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.

Guest favourite

Cottage in Wolfeboro

4.98 out of 5 average rating, 62 reviews

Quaint Wolfeboro Lake Winnipesaukee Lakefront Home

Our charming 2 bedroom cottage is just steps from the water. Complete with private beach, great swimming, deep water docking and amazing views. Don't miss this charming lakeside retreat. Our home features an open kitchen and dining area overlooking the water. Complete with living room and fireplace this cottage is a terrific way to get away from it all. Perfect for families, couples or solo adventurers who want to relax at the lake.

Guest favourite

Apartment in Tuftonboro

4.97 out of 5 average rating, 268 reviews

Apartment CenterTuftonboro minutes from Wolfeboro

This is a spacious lower- level apartment 1000 sq ft in our home . Our guests will have complete privacy with convenience parking . It features a large master bedroom and cozy second bed room. You have a large private kitchen , living room , a bathroom and laundry room . Our area offers many activities as well as shopping in historic down town Wolfeboro. A very short drive to all the best things that Lake Winnipesaukee offers.