Cottage vacation rentals in Wolfeboro

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Top-rated cottage rentals in Wolfeboro

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Guest favorite

A lofted sleeping area features a neatly arranged bed supported by sleek white posts and natural rope. The ceiling showcases wooden planks, contributing to a warm atmosphere. Windows nearby allow natural light to fill the space below, where a kitchen area is partially visible.

Cottage in Laconia

4.94 out of 5 average rating, 110 reviews

Completely updated detached cottage/Paugus Bay!

Enjoy your vacation surrounded by all that Lake Winnipesaukee has to offer! You will enjoy beautiful views of Paugus Bay with the most amazing sunsets and fireworks at the Margate right from the front deck! Completely updated unit! Shared Waterfront deck Conveniently located near shopping, hiking and snowmobile trails, the Naswa Beach Bar, Weirs Beach, FunSpot, and the Margate! Perfect location for Laconia's annual BIKE WEEK and just minutes to the Bank of NH Pavilion for some amazing concerts.

Guest favorite

A hand holds a s'more made with graham crackers and marshmallow, showcasing a toasted treat. In the background, a fire pit is surrounded by large stones, with orange flames flickering. A person is seen sitting in a chair a short distance away.

Cottage in Gilford

4.86 out of 5 average rating, 220 reviews

B: Summer, Lake Winni, Hike, Concerts!,

Walk to concerts! One dog friendly, with host permission, contact host before book, pet fee 75., add pet to reservation. Close to, restaurants, movies, concerts , the lake, and family-friendly activities. You’ll love my place Close to Lake Winnipesaukee, walk to Bank Of NH Pavillion Gunstock, Weirs Beach and Mt. Major, good for couples, solo adventurers, business travelers, and 1 dog friendly. There's a grill, picnic table, fire pit :) Quiet location Gunstock and, winter sports, zip line!

Top guest favorite

Cottage in Acton

4.99 out of 5 average rating, 136 reviews

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake. Swing in the hammock while listening to the cry of the loons. Or enjoy your morning coffee overlooking the quiet cove from your covered porch. 100 feet of shoreline in the calm 3rd basin of the lake. This entire basin is a "no-wake" zone which allows safe swimming for the whole family. Enjoy fishing, search for turtles, or explore beyond the cove using the canoe, kayaks, or paddle boards. Dock your own boat at the 24' aluminum dock.

Guest favorite

Colorful fireworks burst in the night sky above Lake Winnipesaukee, reflecting in the water below. The view is framed by wooden decking and a neighboring boat dock, creating a festive atmosphere during a lakeside celebration.

Cottage in Alton Bay

4.88 out of 5 average rating, 202 reviews

1B Cottage w/kayaks-Lake Winnipesaukee View/Access

Quaint 1 bedroom cottage w/views of Lake Winnipesaukee available year-round. Our deck is literally on Lake Winnipesaukee and a 3 minute walk from the cottage. Here you will be able to enjoy gorgeous views, participate in lake activities such as swimming off our dock, using our kayaks, diving board, etc. The public beach is steps away, along with restaurants, ice cream, water sport rentals, mini-golf & entertainment. Perfect for couples or small family & is pet friendly. Cottage has heat & AC.

Superhost

Cottage

4.79 out of 5 average rating, 483 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Lakefront House, contemporary, amazing views, large deck, private lake beach & dock, steps from house (swimming). Very fast internet, multiple users. Private free parking. Fully equipped kitchen, AC, Smart TV & Modern shower room. Laundry Equipment, all Linen supplied. Sun trap West Facing Deck with loungers for relaxation. Canoe, life preservers & paddles included. 2 Fire pits & Grill. Boat put-in locally. Following cleaning codes: Airbnb & other authorities. Please ask any questions.

Top guest favorite

A hammock is suspended between two trees by the lake, inviting relaxation by the water. Two simple adirondack chairs sit on the sandy ground, offering a place to enjoy the serene view. A canoe is positioned nearby on the shore, surrounded by a natural landscape.

Cottage in Middleton

4.97 out of 5 average rating, 152 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

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 vibrant sunset reflects on the calm lake water, showcasing hues of pink, orange, and purple across the sky. Silhouettes of trees line the shore, and gentle ripples can be seen on the surface, creating a serene atmosphere as day transitions to night.

Cottage in Alton

4.99 out of 5 average rating, 104 reviews

Lake view cottage #2 in Alton Bay on Winnipesaukee

Cottage #174 is one of our 3 cottages. This cozy STUDIO cottage (225 SF ) has a queen size bed/den area , fully equipped kitchen and Full Bath. AC, Wi-Fi , TV with ROKU included. Cottage has its own outside space overlooking the lake with table and chairs making it the perfect setting to relax and enjoy the beautiful lake views. The entire area is fenced in. See other listings Lake view cottage #1 &3 in Alton Bay on Winnipesaukee SEE INFO BELOW ABOUT EXTRA BOAT SLIP

Top guest favorite

A gentle green landscape is viewed from two white Adirondack chairs positioned on the grass. A wooden fence runs through the scene, surrounded by trees that provide ample foliage. The sky is clear and bright, enhancing the tranquil setting.

Cottage in Brownfield

4.99 out of 5 average rating, 250 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Top guest favorite

The exterior of the Carriage House is highlighted by rustic wooden siding and a welcoming entrance. A fire pit is surrounded by seating, creating a cozy outdoor gathering space. Lush greenery frames the area, contributing to a serene atmosphere.

Cottage in Tamworth

4.92 out of 5 average rating, 179 reviews

*Amazing Reviews! *Outdoor Shower -TINY Cottage!

This guesthouse located in the beautiful & historic Tamworth/Chocorua New Hampshire. This house has many special areas to just relax & enjoy nature and the peacefulness this area of the world has to offer! Travel inspired & colorful! You will love both the front and back patios one with a grill & gazebo for outdoor dining in any weather & nicely lit at night & the other with a great porch and fire pit area. The outdoor shower off the porch is just AMAZING!

Guest favorite

The lakeside house reflects beautifully on the calm waters of Sunrise Lake, enhanced by autumn foliage surrounding the property. The scene captures a warm glow from the setting sun, showcasing a serene and peaceful atmosphere by the water's edge.

Cottage in Middleton

4.96 out of 5 average rating, 188 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 favorite

A charming cottage is situated by the water's edge, framed by tall trees. The exterior features a metal roof and flower boxes. A stone pathway leads from the cottage to the shoreline, where a kayak is visible in the background, adding to the serene lakeside atmosphere.

Cottage in Conway

4.95 out of 5 average rating, 346 reviews

20ft from the Water with Mountain View!

This cozy cottage sits 20 ft from Pequawket Pond. We are the only cottage in this association that has 2 floors and directly on the pond. It has a spiral staircase that leads downstairs to the bedroom downstairs with walk out access. We are located within minutes to the Mount Washington Valley and all the amenities the valley has to offer. Ski resorts galore! We also have a kayak and 2 paddle boards available for our guests to use!