Vacation rentals in Winter Harbor

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Top-rated vacation rentals in Winter Harbor

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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, 115 reviews

A Large Vacation Home with hot tub, game room +

AlecRating, 5 stars6 days ago

Very nice place. Great for a family getaway or a gathering with friends/couples. Most bedrooms have attached bathrooms which was great. Game room was very fun. Fooseball table is broken, so if you’re a rare foose junky like myself don’t plan on it. Only disappointment in this great home. Make sure to bring towels or you’ll be taking a trip to Walmart. Otherwise Highly recommend

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

AllisonRating, 5 stars9 months ago

Gisele and her property manager were promptly responsive. The cottage was extremely clean, newly decorated and well appointed. The layout was very comfortable for our family of four. The pools were nice and not overly crowded. The only negatives were: If not taking the trolley or golf cart, the closest pool was a half mile walk with no parking available. The further pool did have parking. Also, no outside water source/hose to rinse off. Plenty of restaurant choices nearby in Wells, Ogunquit and Kennebunkport. Wells beaches were beautiful with easy, affordable parking. Overall a wonderful stay in Wells!

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

ChrisRating, 5 stars2 months ago

We loved the views at the Sommet. The house was spacious enough for all 6 of us without even spending much time in the guest house. We found the beds comfortable and the 3 bathrooms were helpful. The kitchen was pretty well stocked and we ended up eating in 5 out of 7 nights. The Uno, Jenga and Clue were big hits with the whole family. Thanks!

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, 354 reviews

Private In Village, HotTub, 1 bedroom, Fire Place

ShelbyRating, 5 stars1 week ago

First time staying at Scott’s NH North Conway home, and it went very well. He and his team were very responsive to any questions I had and the area was a short drive away. The location of the house was a little confusing to find at first but once we realized it was tucked away, the check in process was easy. The house was great for what we needed for the stay. Thanks!

Top guest favorite

A stone fireplace is framed by wooden beams, adding rustic charm to the space. Firewood is neatly stacked beside the hearth, with a warm fire glowing inside. Two comfortable chairs are positioned nearby, providing a cozy spot to relax.

Condo in Lincoln

4.93 out of 5 average rating, 353 reviews

Cute Studio Apt Resort Lincoln, NH Loon Mountain

DianeRating, 5 stars2 weeks ago

Rick was an exceptional host. This is I believe our third or second time staying at one his places and we of course loved it! Rick was very good about messaging us to make sure we were all checked in and had everything we needed. We would absolutely stay with Rick again and recommend him to our loved ones and friends! Thanks again Rick!

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

MeganRating, 5 stars1 month ago

Great location close to Ragged Mountain for winter sports. Comfortable home, lots of beds for kids (wish the homes we had stayed in when our kids were little were as well stocked with toys and a fun toddler bed!) Also loved that the pantry was stocked-we unexpectedly got to have fresh baked muffins with breakfast.

Guest favorite

A private balcony features a round table and four chairs, overlooking colorful autumn trees with sunlight filtering through the clouds. The scene captures a peaceful outdoor space, inviting guests to relax and enjoy the surrounding natural beauty.

Condo in Lincoln

4.92 out of 5 average rating, 168 reviews

Cute Resort Studio Apt with Pool, hot tub at Loon

LuciaRating, 5 stars2 weeks ago

Ricky’s place was amazing! Fabulous location just a 10 minute drive from the Franconia Loop Trail (where we hiked). Big studio apartment with a full kitchen & bathroom. Very cute woodsy decor inside & there is a lovely common area in the apartment with board games & and a fire for after dinner activities! We had such a great time!

Guest favorite

A spacious living area features a comfortable chaise lounge and an open layout connecting to a dining area with modern lighting. A built-in bookshelf filled with colorful books adds a touch of character to the room, while hardwood flooring enhances the overall warmth.

Home in Ogunquit

5 out of 5 average rating, 26 reviews

Hoyts Ahoy

JulieRating, 5 stars1 month ago

We had a wonderful weekend celebrating St. Patty’s Day up in Ogunquit. The property was everything we had hoped for in a rental. Everything was comfortable and clean. The house is spacious and a great place to get your day started. You can’t beat the location! Off the beaten path, but a few minutes of walking to downtown. The host was super responsive to my questions. I would absolutely stay here again.

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Other great vacation rentals in Winter Harbor

Superhost

Home in Tamworth

4.82 out of 5 average rating, 97 reviews

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

KarenRating, 5 stars3 days ago

We had a wonderful time. The house was perfect. It was a short walk to the lake. Very peaceful and quiet. Loved having 3 full bathrooms. It was a short drive to Conway for shopping and restaurants.

Top guest favorite

Apartment in Bartlett

5 out of 5 average rating, 22 reviews

Large Family Apartment

KarenRating, 5 stars1 month ago

Kevin's place was great! Very clean, comfortable and in good area as we stayed for a week of skiing. Easy to get to Attitash ski resort and quick drive to Wildcat Mountain. Kevin was easy to communicate with and would return again next year for sure!

Superhost

A charming log cabin with a gabled roof is set against a clear blue sky. Large windows enhance the natural light and provide views of the surrounding trees. A spacious deck features outdoor seating, surrounded by stone steps leading to the lush green yard.

Cabin in Bartlett

4.92 out of 5 average rating, 179 reviews

Mountain View Retreat, Near skiing, shopping

JaimeRating, 5 stars4 months ago

We absolutely loved our stay! Plenty of room for 8 guests (and more!!) in a beautiful setting. There was many helpful amenities, like kitchen items, and plenty of towels. The location is perfectly centered to many popular things to do. James was always very responsive to questions left clear instructions. We highly recommend staying here and hope to do so again in the future.

Superhost

A cozy outdoor seating area is showcased with two bright green chairs positioned around a circular fire pit. A textured blue and green mat is laid beneath, while surrounding trees create a serene backdrop, enhancing the peaceful ambiance of the space.

Townhouse in Bartlett

4.85 out of 5 average rating, 105 reviews

Spacious Family Vaca Storyland*Saco*Close to all!

JoanneRating, 5 stars2 months ago

Great place to stay. The basement space for the kids is great, they each had their own bedroom but could hang in the common space. Golden Tee was a HIT! Centrally loacated to multiple ski mountains. Plenty of room to spread out and get comfortable!

Guest favorite

A spacious deck is highlighted, featuring a circular table and two chairs, with a scenic view of surrounding greenery and distant mountains. Sunlight bathes the area, creating a bright and inviting outdoor space for relaxation.

Home in Haverhill

4.96 out of 5 average rating, 45 reviews

White Mountains Cottage w/ Mountain & Lake Views!

MelissaRating, 5 stars2 months ago

Cute and cozy home in New Hampshire, we experienced a snow storm and had a blast sledding down the hill for both adults and kids. Peaceful and beautiful scenery.

Guest favorite

A covered hot tub is displayed on a wooden deck, surrounded by lush greenery. The bubbling water invites relaxation, while colorful chairs in the background suggest a cozy outdoor gathering space.

Home in Freedom

4.9 out of 5 average rating, 94 reviews

Our Mountain Retreat – Lake Ossipee Access

FinRating, 5 stars1 month ago

Paula’s was the perfect spot for a weekend trip with a group of friends for my birthday! It had plenty of sleeping spots for us and was very comfortable, and we really loved the hot tub. They were such responsive and communicative hosts as well, and offered us a flexible late check-out. Thank you!

Guest favorite

A stone pathway leads to a set of wooden steps, framed by lush greenery. Flanking the stairs are well-maintained bushes and decorative lanterns, enhancing the inviting approach to the entrance of the home.

Home in Holderness

4.9 out of 5 average rating, 10 reviews

Beautiful Home away from Home

StefanieRating, 5 stars2 months ago

My friends and I had a wonderful stay at this house hosted by Byron Property Management. They had snacks waiting for us when we arrived, Christina was kind and quick to respond when we had a question, and the house was exactly what was demonstrated in their advertisement. We are excited to come back next year and hopefully make this an annual trip at this property!

Top guest favorite

An open living area is showcased with large windows allowing natural light to illuminate the space. A cozy sectional sofa faces a modern TV, while a wooden dining table and chairs are positioned nearby. Decorative elements enhance the room's welcoming feel.

Home in Thornton

5 out of 5 average rating, 9 reviews

Spacious Private Home in White Mountains-Loon-Owl

KristenRating, 5 stars1 month ago

The house was perfect for a bigger group and had so much space! Great location and amenities-everything was labeled which was super helpful! The location was great for surrounding ski mountains (20 min to several), as well as other activities. Owners were very communicative and easy to reach if needed. Would love yo rent again!

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Vacation rentals in Winter Harbor

Top-rated vacation rentals in Winter Harbor

Vacation rentals for every style

Popular amenities for Winter Harbor vacation rentals

Other great vacation rentals in Winter Harbor

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