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.

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Superhost

A welcoming cabin is situated down a gravel driveway surrounded by tall trees. Warm light spills from the windows, creating a cozy ambiance as dusk settles. A lantern beside the pathway adds a gentle glow, inviting guests toward the entrance.

Home in Conway

4.83 out of 5 average rating, 114 reviews

A Large Vacation Home with hot tub, game room +

My place is close to family-friendly activities, skiing, snowboarding, golf, shopping, hiking, restaurants, night life, shoe shoeing, ice skating, sleigh rides, tubing, Saco River tubing/canoeing, Echo Lake, Gondloa rides to summit, mini golf much more. You’ll love my place because of the quiet neighborhood, comfy beds, the kitchen, the hot tub and fireplaces and the space for large reunions and gatherings . My place is good for couples, business travelers, families (with kids), and big groups.

Superhost

A charming cottage is nestled among vibrant trees, displaying shades of orange and yellow. Outdoor seating is provided by several blue chairs arranged on a manicured lawn, with a pathway leading to a sunroom that features numerous windows allowing natural light to flood the space.

Home in Wells

5 out of 5 average rating, 3 reviews

"In Tempore" Cottage

Relax in this calm, stylish space. New for 2024, "In Tempore Cottage" at Summer Village! Downtime at the right time! Enjoy the many amenities: tennis, pickle ball, putting green, ball fields that provide unobstructed stargazing on clear nights, heated pools, hot tub, indoor gym, playground. Ride the resort trolley in season. Bike, or walk along peaceful forests. New! Discounted rates for fall! **Linens and towels not included. Guests must supply their own or rent from Cottage Linens**

Guest favorite

A stone fireplace with a modern design is centered against a rustic wall, featuring stacked firewood on either side. The warm glow of the fire illuminates the surrounding area, complemented by natural wood beams on the ceiling.

Condo in Lincoln

4.96 out of 5 average rating, 160 reviews

Gorgeous River & Loon Mountain View Studio Condo

Cozy Studio Condo in hotel resort community sleeps 3. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy Lovely views of the mountain and Pemi River! You'll love the nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

Guest favorite

A fire pit surrounded by four wooden Adirondack chairs is set against a gravel area. The rustic lodge can be seen in the background, framed by trees displaying autumn colors and string lights. A peaceful and inviting outdoor space is highlighted.

Home in Jackson

4.98 out of 5 average rating, 54 reviews

The Sommet-Magical Views- Main house+Guest cottage

Welcome to The Sommet in Jackson, NH – a mountain getaway lodge - MAIN HOUSE with a GUEST COTTAGE. Picturesque views, local restaurants, and endless recreation await you at this 3-bedroom, 3-bath vacation rental! Located within minutes of Mt Washington, and the multiple ski areas. Mountain biking and hiking locations within minutes’ drive. Saco River provides outdoor recreation like canoeing, kayaking, tubing and rafting. Swimming, fishing could make this a perfect summer getaway.

Superhost

A natural rock formation features small waterfalls cascading into a clear pool. Surrounding greenery adds a touch of nature, while guests are seen enjoying the water. Sunlight reflects off the rocks, creating a warm atmosphere.

Home in Conway

4.84 out of 5 average rating, 351 reviews

Private In Village, HotTub, 1 bedroom, Fire Place

PLEASE DO NOT BOOK PEAK HOLIDAYS/WEEKENDS IN ADVANCE as we try to rent the entire house 1st. We book this listing as a 1 bedroom ONLY. Directly in the village! yet tucked away, private YARD, HOT TUB, fireplace, new furniture, cozy beds and & linens. WALK to restaurants, Saco River, Golf, Village Green, Rec Center, Whitaker Woods, scenic train station, coffee shops, stores, skating, Cranmore & nightlife. Enjoy Kayaking, skiing, adventure parks, skiing, story land, hiking, etc.

Top guest favorite

A covered porch area is furnished with two white wicker chairs, accompanied by decorative pumpkins and colorful autumn leaves. String lights are draped along the railing, creating a welcoming outdoor space that invites relaxation in a residential setting.

Apartment in Northfield

4.96 out of 5 average rating, 78 reviews

The Lady Grand at Northfield

Comfy, Private, First Floor Appartment. Self Check-In, Parking New England vacation rental within walking distance to our scenic historic main street. Centrally located to bike parks, white water park, numerous skiing and hiking options. In an hour's drive, it is possible to be at the shore, in the mountains or one of our great cities! Our guest suite has a private entrance to a mud room and is fully furnished, full kitchen and bath and can sleep up to 6 people.

Top guest favorite

A serene river flows through rugged granite formations, surrounded by vibrant autumn foliage. Tall trees flank the banks, showcasing a mix of greens, yellows, and oranges. The distant mountains rise gently under a clear sky, creating a tranquil natural landscape.

Condo in Lincoln

4.93 out of 5 average rating, 352 reviews

Cute Studio Apt Resort Lincoln, NH Loon Mountain

Quaint Studio Apartment, Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Skiers & snowboarders enjoy the Free Shuttle to Loon Mountain Ski Resort only minutes away. Great area dining, and outdoor activities, indoor pool, outdoor pool, Sauna, Jacuzzi and game room make this is a great vacation location for your family. Great restaurants within walking distance.

Superhost

A cozy loft bedroom features a wooden ceiling with exposed beams. A spacious bed is positioned centrally, flanked by two bedside lamps on dark nightstands. Light filters through a window adorned with curtain panels, illuminating the rustic wooden walls and framed artwork.

Cabin in Woodsville

4.88 out of 5 average rating, 317 reviews

Cabin Getaway, Pool Tb, Darts, Poker Tb, ATV Trail

Log cabin getaway in White Mountains, NH. Located in Mountain Lakes community, it is a perfect location from which to enjoy outdoors. You can fish, swim, hike, ski and then come back to a comfortable home. Sit on the deck and pick at the mountains or enjoy a get together by the big fire in the yard. Easy walk to the lakes. Close to trails for ATV and snowmobiles. Visit nearby towns of Lincoln, Littleton, Franconia with lots of restaurants and activities.

Superhost

A spacious lawn is surrounded by trees, providing a serene backdrop for outdoor activities. Comfortable seating is arranged near a firepit, while a rustic barn stands in the distance. A well-maintained walkway leads to the entrance of the charming red house.

Cottage in Hill

4.98 out of 5 average rating, 87 reviews

The red house

Charming Country Retreat in Hill, NH - Perfect for Families and Groups Welcome to our serene home in the charming town of Hill, New Hampshire! Nestled on 12 scenic acres, this inviting home offers the perfect blend of tranquility and adventure for families and groups looking to escape the hustle and bustle. Feel free to reach out if you have any questions or need additional information. We’re here to help make your stay perfect!

Guest favorite

Condo in Lincoln

4.92 out of 5 average rating, 167 reviews

Cute Resort Studio Apt with Pool, hot tub at Loon

Relax with the whole family at this peaceful place to stay. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

Guest favorite

Two refurbished cabins are nestled among tall trees, reflecting gently on the calm waters of a basin. The cabins feature large windows and outdoor seating areas, offering serene views of the surrounding greenery.

Cabin in Wolfeboro

4.97 out of 5 average rating, 130 reviews

Northern Lights

One of two relaxing refurbished cabins located on Goodwin's basin. You can watch the turtles right from the comforts of the livingroom. Located right off of the Bridge Falls Path, making it convenient for biking or walking to town. Quiet clean beach located on Crescent Lake for you to enjoy with the kids, and access to a boat dock upon booking. Additional Occupancy tax must be paid at or prior to check-in.

Guest favorite

A group of wooden Adirondack chairs is arranged on a gravel surface in a snowy outdoor setting. The back of a two-story home with a screened-in porch is visible, surrounded by trees, inviting relaxation and gathering in nature.

Home in Intervale

4.91 out of 5 average rating, 70 reviews

Honey Bear house Close to all Storyland & village

Must bring Bathing towels, We will supply everything else. ALL Major holidays 3 night min. !! 25 and older to stay .Disinfected. Cozy-Clean- spacious and great location. Perfect for larger families.. Location is the best part as you feel like you are away from it all but close to all attractions. This home is close to the village-storyland and the white mountains. Must bring towels, we provide sheets.