Cottage vacation rentals in Wolfeboro

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Top-rated cottage rentals in Wolfeboro

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Guest favorite

A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.

Cottage in Northwood

4.93 out of 5 average rating, 121 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Top guest favorite

A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.

Cottage in Acton

4.99 out of 5 average rating, 146 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

A quaint cottage exterior is depicted with a backdrop of vibrant fall foliage. The structure features light gray siding and a welcoming front door, while the calm waters of Lake Winnipesaukee are visible in the background.

Cottage in Alton

4.88 out of 5 average rating, 208 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.

Guest favorite

A charming historic house is surrounded by mature trees, showcasing a white exterior and a welcoming front porch with rocking chairs. A well-maintained picket fence frames the property, while colorful flower arrangements are seen near the windows, enhancing the peaceful outdoor setting.

Cottage in Plymouth

4.91 out of 5 average rating, 407 reviews

Plymouth's Historic Doll House; A tiny house

The Doll House has everything you’ll need at under 700 square feet. This fully-outfitted, historic, full-house rental has a complete kitchen, living room, two-bedrooms, bath, back sitting room, front farmer's porch and beautiful gardens and sitting areas. The Doll House is within easy walking distance to the Town Common, great restaurants and shopping, the Flying Monkey, and PSU. We are just a few minutes' drive to the Barn on the Pemi and Holderness School. NH Rooms Tax; License #059528.

Superhost

A serene view of a lake surrounded by trees, reflecting the clear blue sky. The water's surface appears smooth, indicating calm conditions. The landscape features distant houses among the trees, contributing to a peaceful natural setting.

Cottage in Freedom

4.79 out of 5 average rating, 490 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 cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.

Cottage in Middleton

4.97 out of 5 average rating, 157 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.

Superhost

A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.

Cottage in Parsonsfield

4.87 out of 5 average rating, 168 reviews

RiverPine Retreat - Clean & Bright Waterfront Home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Guest favorite

The custom log home is surrounded by lush greenery, showcasing a wrap-around deck with multiple seating areas. A hammock is positioned in the foreground, inviting relaxation. The sloped driveway leads to the entrance, enhancing the natural, tranquil setting.

Cottage in Meredith

4.85 out of 5 average rating, 204 reviews

Log Home Meredith NH Pet Friendly Custom Fire-Pit

I AM BACK MANAGING BOTH PROPERTIES 2025! :) FOUR NIGHT MIN STAY July and August! Holiday weekends 3 night minimum. Down the road from Lake Winnipesaukee in Meredith NH! COZY 1300 foot custom log home, pet friendly up to two dogs, custom outside fire-pit, wrap around deck, 3 miles to downtown Meredith NH, Near restaurants, Hiking, beaches, Spa's, breweries, etc. Enjoy a relaxing getaway with your family and friends. local town beach. No smoking in the home, no fireworks, no parties

Guest favorite

The sandy beach area features several white adirondack chairs arranged for relaxation. Gentle waves lap at the shoreline, where boats are anchored in the distance. A staircase leads up from the beach to a grassy area, surrounded by trees, under a clear sky.

Cottage in Wolfeboro

4.96 out of 5 average rating, 116 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.

Guest favorite

A well-maintained lawn leads to a serene lake view, with a flagpole displaying an American flag. A covered boat dock and several trees line the water's edge, while a pet can be seen on the grass, contributing to the tranquil atmosphere.

Cottage in Moultonborough

4.95 out of 5 average rating, 104 reviews

The Lake house

Enjoy the southern exposure, a sugar sand walkout beach, an L-shaped dock, and classic Lake Winnipesaukee construction. The open concept includes a full kitchen and a living room. The spacious bathroom also includes a washer and dryer. It has one private bedroom, and a ships ladder guides you to a loft containing additional sleeping space, with a catwalk to a private balcony overlooking the lake. This property has a detached bunkhouse with two full-sized beds and a ¾ bath.

Guest favorite

The exterior of a quaint cottage is visible, featuring a tan façade and a front door framed by a simple porch with steps leading down. A fenced area surrounds a small outdoor space with a shaded table and chairs, enhancing the private setting.

Cottage in Alton

4.97 out of 5 average rating, 111 reviews

Lake view cottage #174 in Alton Bay-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 cozy cottage is framed by lush greenery and colorful landscaping, featuring a welcoming front porch and a sunroom with large windows. A picnic table is positioned nearby, inviting outdoor relaxation. The property is set against a backdrop of trees, contributing to a private and serene environment.

Cottage in Brownfield

4.99 out of 5 average rating, 254 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.