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Holiday houses in Wolfeboro

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Quick stats about holiday rentals in Wolfeboro

  • Total holiday rentals

    Explore 210 holiday rentals in Wolfeboro

  • Nightly prices starting at

    Wolfeboro holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 7,680 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    200 of Wolfeboro holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Lake access, Gym and BBQ across Wolfeboro rentals

  • 4.9 Average rating

    Wolfeboro stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Wolfeboro

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The spacious living area features light green striped walls, complemented by a wooden floor. Two comfortable sofas are positioned around a coffee table, with decorative pillows adding texture. A dining table is visible in the background, and a staircase leads to the upper level, enhancing the open concept layout.
Home in Wolfeboro

Lake Access + Kayaks+Arcade+Bike Path+Private deck

Welcome to the Striped Loon! Our newly updated 2bd/1ba cottage is just steps away from Crescent Lake (great for kayaking) and Cotton Valley Rail-trail walking/bike path leading directly into downtown. Perfect for families , small friend groups, or couples our home offers the below amenities to enhance your stay! -Beach pass & towels, chairs, blanket -Two player arcade, Board games, pickleball set -TV for streaming -Private deck with grill, dining area and deck fire pit -Kayaks, lifejackets

4.94 out of 5 average rating, 50 reviews
Guest favourite
A serene waterfront view features a calm bay dotted with individuals enjoying various water activities. Paddle boards and kayaks are in use on the gentle water, while a small dock extends into the lake. Lush greenery surrounds the scene, creating a tranquil atmosphere.
Cottage in Wolfeboro

🌟Winni Cottage beach, dock, kayaks, SUP & more! 🌈🍸

Great waterfront cottage on Wolfeboro’s Back Bay! Includes 5 kayaks, 2 canoes, a paddleboard & rowboat. 3 bedrooms, plus indoor & outdoor hot showers. Large deck, big grassy lawn, and cozy campfire area. Calm, protected bay—perfect for beginner paddlers. 40-ft dock, beach area, & swim platform on a mooring. Bring your boat or rent one to access main lake under the bridge. Just an 8-minute walk to town! Bring bikes explore scenic trails. A peaceful, relaxing retreat with all the lakefront fun.

4.91 out of 5 average rating, 97 reviews
Guest favourite
Home in Wolfeboro

Gram's House

Enjoy easy access to town from this historic home. Relax on the deck overlooking Wolfeboro Bay. Enjoy a swim whenever you want. There are 4-season activities in the area: bike, hiking and ski trails close by. Private beach, raft (no dock), canoe/kayaks, and beach toys. Great gathering place: our family has enjoyed many special events here! HOWEVER, if you are looking for a place to have loud parties, this is not for you. This rental is in a neighborhood and we respect our neighbors.

4.85 out of 5 average rating, 20 reviews
Top Guest favourite
A serene view of Mirror Lake presents a tranquil morning scene, where mist rises gently from the water's surface. Two chairs are positioned in the foreground, inviting relaxation. Soft sunlight glimmers on the lake, enhancing the peaceful ambiance of the natural surroundings.
Home in Tuftonboro

Peaceful Lakefront Retreat

Rest, relax and recharge at this tranquil waterfront getaway on stunning Mirror Lake. Unplug from the hurry and enjoy this entire lakefront home in the privacy of a quiet street just minutes from downtown Wolfboro. Dining area, living space, kitchen and two bedrooms offer all the comforts you need with stunning lake views. Cozy cabin-like downstairs den has entertainment space, tables and seating for movies and games. Perfect spot for a quiet getaway to connect with friends, family and self.

4.98 out of 5 average rating, 48 reviews
Top Guest favourite
A bedroom features a spacious bed dressed in neutral linens, complemented by a decorative pillow. A nightstand holds a lamp with a soft light. Natural light filters through vertical blinds, enhancing the serene atmosphere. A framed black-and-white photograph reflects a peaceful lake scene.
Guest suite in Wolfeboro

Downtown, Cozy, Cute, and Convenient!

Walk just one block to the heart of downtown Wolfeboro, the "Oldest Summer Resort in America". Dine, shop, visit art galleries, or just relax in the park overlooking the docks on Wolfeboro Bay. Take the Mt Washington Ferry for a Lake Winnipesaukee ride or Molly the Trolley hop on/off tour. The rail trail is close by and a playground is just steps away for the little ones. Also, Wolfeboro’s best Mexican restaurant, coffee shops, Hunter’s grocery and Walgreens are all just a short walk away!

4.88 out of 5 average rating, 207 reviews
Top Guest favourite
A cozy living space features a high, vaulted wooden ceiling with large triangular windows showcasing lake views. Two hanging chairs are positioned beside a plush sofa, and a coffee table sits on an area rug, enhancing the inviting atmosphere.
Home in Wolfeboro

Luxury Lakehouse| Sunsets| Cen. Air| Private Dock

Crystal clear Rust Pond contemporary waterfront home with picturesque lake views from every angle and multiple decks. Your vacation home has central AC for hot days and a cozy gas fireplace and central heat for chilly nights. Rust Pond is an oligotrophic lake with excellent swimming, SUP boarding, kayaking, fishing, etc. The home offers privacy in a peaceful lakeside setting, yet is just 10 mins from Wolfeboro downtown restaurants, farm to table fare, art galleries and boutique shopping.

4.99 out of 5 average rating, 80 reviews
Top Guest favourite
A dining area features a rustic wooden table surrounded by two woven chairs. Light from a pendant lamp highlights floral artwork on the wall. Beyond, a cozy living space is visible, furnished with a pink sofa and a green table, framed by a large window.
Guesthouse in Wolfeboro

Remnant House Cottage Suite

Come and enjoy a relaxing stay at Maple Hill Cottage suite and experience New England seasons and all they have to offer, 5 minutes from Lake Winnipesaukee and downtown Wolfeboro, 3 minutes to Abenaki Ski Area and 30 minutes from Gunstock Ski Resort. Nestled amongst Sugar Maples on 13 acres attached to the host's home with separate private entrance. You are sure to enjoy a cozy retreat. Apartment boasts King size bed, custom kitchen with washer/dryer, full bath and fast internet.

4.98 out of 5 average rating, 90 reviews
Top Guest favourite
A charming multi-story house with a distinctive tower is depicted, featuring several balconies and large windows. The exterior is painted in soft green, complemented by red accents. A well-maintained lawn is visible in the foreground, with several white Adirondack chairs arranged neatly.
Condo in Wolfeboro

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.

4.96 out of 5 average rating, 168 reviews
Top Guest favourite
Cottage in Wolfeboro

Cozy Wolfeboro Getaway | Lake, Ski & Fireplace

Welcome to Lake a Dream - your cozy, family-friendly Wolfeboro getaway in EVERY season! Enjoy our neighborhood beach just a 5-minute walk away or explore charming downtown Wolfeboro, only 5 minutes from the cottage. Winter is just as magical! Ski at Wolfeboro’s hidden gem, Abenaki Ski Area, skate, snowshoe or simply cozy up by the fireplace with hot cocoa & family games. Looking for a bigger mountain day? Gunstock & King Pine are nearby too!

4.97 out of 5 average rating, 145 reviews
Top Guest favourite
Red Adirondack chairs surround a fire pit on sandy ground, facing a serene lakeside view. Towering trees provide shade, and the calm water reflects the clear blue sky, creating an inviting atmosphere for gatherings and relaxation.
Home in Wolfeboro

Lakeside Getaway - Lake Access/PrivateDock/Firepit

Escape to this cozy lakeside retreat with direct access to Crescent Lake - perfect for swimming, kayaking, or simply enjoying the view. Bring your own boat and take advantage of the private dock, offering effortless access to the water for fishing, cruising, or sunset rides. In the evening, gather around the fire pit and unwind under the stars.​ This house is ideal for couples, families, or groups seeking comfort, nature, and connection.

4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Wolfeboro

Family Retreat in Wolfeboro: 5BR/3BA, Lake Views

A new opportunity for your large family or reunions to stay in “The Oldest Summer Resort in America” in a historic home located a few minutes from downtown. This 1870’s home was turned into “The Oaks” in the early 1900’s as an Inn for visitors over a hundred years ago to take in the Crescent Lake view. Your gathering will enjoy the beautiful character of the old Inn while utilizing modern amenities.

5.0 out of 5 average rating, 6 reviews
Top Guest favourite
The exterior features a charming blue barn-style structure with wooden sliding doors, welcoming guests with a 'Welcome' sign. A deck is visible on the right leading down to the water, with scenic views of Crescent Lake in the background, framed by trees.
Barn in Wolfeboro

The Barn at Crescent Lake

Welcome to Wolfeboro, New Hampshire! Our barn is located just outside of downtown Wolfeboro, filled with multiple shops and eateries! Our home is on Crescent Lake, with private beach access and a dock with a boat slips if needed. The home is located off of Wolfeboro's Cotton Valley Rail tail, a peaceful walking path that begins in downtown and passes through several towns!

4.96 out of 5 average rating, 132 reviews

Popular amenities for Wolfeboro holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Wolfeboro's top sights

Lake Winnipesaukee

167 locals recommend

Lake Wentworth

10 locals recommend

Wolfeboro Bay

28 locals recommend

Pavilion

26 locals recommend

Rattlesnake Island

3 locals recommend

Wentworth State Park

19 locals recommend

Other great holiday rentals in Wolfeboro

Guest favourite
A family lake house is positioned over the water, surrounded by lush trees. The two-story structure features multiple decks, providing space for outdoor activities. Colorful kayaks and paddleboards are visible along the dock, reflecting a peaceful lakeside ambiance under a partly cloudy sky.
Cottage in Alton

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay

4.94 out of 5 average rating, 87 reviews
Guest favourite
Home in Wolfeboro

Cozy Lake Cabin with Jacuzzi Tub

4.82 out of 5 average rating, 22 reviews
Guest favourite
Home in Wolfeboro

Wolfe House at Winni

5.0 out of 5 average rating, 12 reviews
Guest favourite
A spacious bedroom is presented, featuring a large bed with a decorative headboard and a light comforter. A ceiling fan is visible above, and a seating area is provided with a patterned chair. A doorway leads to a bathroom, and natural light comes from a nearby window.
Loft in Wolfeboro

Spacious, Dog Friendly Rental in Wolfeboro NH!

4.76 out of 5 average rating, 76 reviews
Top Guest favourite
A cozy entryway features a welcoming porch with a hanging fern plant beside a large window. An adirondack chair is set against the wall, positioned near a wooden side table. A doormat greets guests at the entrance, contributing to the inviting feel of the space.
Cottage in Wolfeboro

King’s Cottage PERFECTLY LOCATED!

4.99 out of 5 average rating, 90 reviews
Top Guest favourite
A cozy living area displays a light sofa and an accent chair, both complemented by soft throw pillows. A coffee table sits centrally beneath a ceiling fan. Light streams in through the windows, highlighting the warm wood tones of the space and the adjoining dining area.
Home in Wolfeboro

Quaint Wolfeboro NH Home.

4.98 out of 5 average rating, 44 reviews
Top Guest favourite
Apartment in Wolfeboro

Comfy Cozy Downtown Apartment brand new 2 bedroom

5.0 out of 5 average rating, 43 reviews
Top Guest favourite
A side view of a charming green cottage is presented, featuring white trim and multiple windows that allow natural light inside. The surrounding area is lush with greenery, and a well-maintained path leads up to the entrance.
Bungalow in Wolfeboro

2 Bedroom Guest Cottage. Close to town

4.95 out of 5 average rating, 109 reviews

When is the best time to visit Wolfeboro?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$327 AUD$311 AUD$310 AUD$262 AUD$327 AUD$379 AUD$384 AUD$376 AUD$323 AUD$323 AUD$316 AUD$300 AUD
Avg. temp-5°C-4°C1°C7°C14°C19°C22°C21°C16°C10°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Wolfeboro?

    Many visitors choose stays near downtown Wolfeboro for walkable shops, dining, and lake access. Vacation homes and rentals around the lakeshore are frequently suggested for those seeking quieter surroundings. Areas near the town center or with waterfront views are popular among travelers.

  • What are the best things to do in Wolfeboro with kids?

    Kids can spend time at public beaches along Lake Winnipesaukee, bike or walk along the Cotton Valley Rail Trail, and enjoy casual treats from ice cream shops. Playground spaces and outdoor recreation are often recommended for families looking to relax or adventure together.

  • What are some of the best things to do in Wolfeboro?

    Explore Lake Winnipesaukee by kayak or tour boat, stroll the Cotton Valley Rail Trail, or browse exhibits at the local museums. Seasonal art fairs, live music, and relaxing in lakeside parks are frequently suggested. Wolfeboro encourages both recreation and cultural experiences.

  • How is the weather in Wolfeboro?

    Wolfeboro has cold winters with snow, averaging 13–32°F (−11–0°C) in January, and mild summers around 59–83°F (15–28°C) in July. Spring and fall bring changing foliage and variable rain, so packing a rain jacket and layers is useful year-round. Weather can shift quickly near the lake.

  • When is the best time to visit Wolfeboro?

    Summer is often recommended for waterfront activities, outdoor events, and mild temperatures. Early fall draws visitors for colorful foliage and quieter streets, while winter appeals to those who enjoy snow sports. Each season has its own distinct atmosphere around the lake.

  • What are the best places to visit in Wolfeboro?

    Popular places include Lake Winnipesaukee for water activities, the Wright Museum of World War II for regional history, and the New Hampshire Boat Museum. Visitors frequently explore downtown shops, art galleries, and peaceful waterfront parks. The town center blends history, art, and recreation.

  • What are some hiking trails in Wolfeboro?

    Explore forested trails in the Sewall Woods Conservation Area or stroll along the Cotton Valley Rail Trail for a gentle route. Mount Major nearby provides options for those seeking broader vistas. These areas showcase Wolfeboro’s mix of woods and water.

  • What are some family activities we can do in Wolfeboro?

    Families often explore beaches on Lake Winnipesaukee, walk or bike the Cotton Valley Rail Trail, and enjoy picnics in local parks. Boat tours, casual lakeside dining, and playgrounds add to the welcoming atmosphere throughout town.

  • What are some of the best day trip ideas from Wolfeboro?

    Day trips often include exploring small New Hampshire villages, hiking in the Lakes Region, or visiting local farm markets. The White Mountains and historic mill towns offer varied scenery nearby. Nearby nature preserves provide further adventure opportunities.

  • Are there any pet friendly accommodations available in Wolfeboro?

    Many vacation rentals and cottages in Wolfeboro welcome pets, especially those around the lakeshore and in residential neighborhoods. Trails and parks often have pet-friendly spaces, making it easier to explore with your companion. Check each property’s policies before booking.

  • What are some local tips for visiting Wolfeboro?

    Bring layers for shifting weather and comfortable shoes for exploring waterfront paths. Many spots are locally owned, so ask about house specials or seasonal recommendations. Early mornings on the lakefront are often peaceful and scenic.

  • What is Wolfeboro known for?

    Wolfeboro is known for its lakeside setting on Lake Winnipesaukee, New England charm, and outdoor recreation. The area’s historic streets, museums, and community events are frequently highlighted. It is often appreciated for its welcoming atmosphere and scenic beauty.

  • What are the best hidden gems to explore in Wolfeboro?

    Explore the New Hampshire Boat Museum for insights into regional lake life, and browse local art galleries for works by area artists. Quiet lakefront parks, as well as independently run shops and markets, are frequently suggested for a different perspective on Wolfeboro’s culture and history.

  • What are the best foods to try in Wolfeboro?

    Wolfeboro’s eateries frequently suggest fresh New England seafood, house-made ice cream, and traditional maple treats. Lakeside cafés and local bakeries highlight seasonal flavors. Locally sourced produce is common during the warmer months.

  • What should I bring for a trip to Wolfeboro?

    Pack clothing layers for changing weather, comfortable shoes for walking, and swimwear if you plan to enjoy the lake. A rain jacket or umbrella is useful in spring and fall. In colder months, warm outerwear and sturdy boots are suggested for outdoor activities.

  • What is the nightlife in Wolfeboro like?

    Wolfeboro has a relaxed nightlife scene, with neighborhood taverns, brewpubs, and seasonal lakeside patios. Live local music and open-air events are popular in the warmer months. The town’s vibe leans toward laid-back gatherings and social evenings.

  • What are the most popular events or festivals in Wolfeboro?

    Wolfeboro has a lively calendar, with outdoor summer concerts, art shows, and craft fairs often recommended. Holiday parades and winter festivals draw crowds, especially around national holidays. Community events by Lake Winnipesaukee are a seasonal highlight.

  • Are there family friendly vacation rentals in Wolfeboro?

    Wolfeboro has many family-friendly vacation rentals, especially around the lakeshore, near parks, and in quiet neighborhoods. Spaces often include kitchens, multiple bedrooms, and outdoor areas for group activities. Families appreciate convenient access to playgrounds and beaches.

Destinations to explore