House holiday rentals in Wolfeboro

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Top-rated house rentals in Wolfeboro

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

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Top guest favourite
A cabin with a spacious deck overlooks a natural setting. The structure features large windows and a bright red umbrella set over a wooden table. Surrounding green trees and shrubs create a serene environment, while a canoe rests nearby on the ground.
Home in Wolfeboro
4.99 out of 5 average rating, 136 reviews

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Top 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
4.96 out of 5 average rating, 25 reviews

Lake Access + Kayaks + Arcade + Bike Path + 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

Guest favourite
A bright and airy bathroom features a freestanding bathtub and a walk-in shower with clear glass doors. Wood-paneled walls complement a light wood floor. Accessory details include a small shelving unit with neatly arranged towels and a potted plant on a side table.
Home in Acton
4.97 out of 5 average rating, 253 reviews

The ZEN welcomes you, your home away from home.

The goal is for you to relax, recharge, enjoy & breathe. We offer a private 3 person HOT TUB , seasonal outdoor warm shower& chiminea firepit , infrared SAUNA, 72" freestanding bathtub for the ULTIMATE spa experience. King bed with an adjustable & vibrating bed base. The cozy 600 sqf home is equipped with everything your heart could desire. Artistic Design around every corner. BOHO swings on the private porch. We abutt a 13 ac conservatory land with walking & hiking trails off the backyard.

Top guest favourite
A vibrant fireworks display illuminates the night sky above the water, reflecting colorful patterns on the lake's surface. Nearby boats and structures are softly lit, creating a festive atmosphere. In the foreground, a wooden deck with a chair provides a vantage point for enjoying the view.
Home in Alton
4.91 out of 5 average rating, 169 reviews

Lake Winnipesaukee House with Slip, Kayaks, Views!

Come build memories at this beautiful lake front house with its own dedicated deep water slip (across the street), a large deck on the water with diving board, and another deck attached to the house. A sandy public beach , restaurants, and Mt Washington boat stop are only steps away. This well-kept house has an open concept, fully applianced modern kitchen, a 55" smart 4K Roku TV, 1 gig fiber internet/wi-fi, a jacuzzi in one of the bathrooms, grill*, all the comforts of home, and so much more.

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
5 out of 5 average rating, 31 reviews

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.

Top guest favourite
A two-story home is set against a backdrop of lush greenery. The structure features a covered porch with large windows, and a well-maintained lawn leads up to the entrance. A driveway is visible, along with a garage at the base of the house.
Home in Glendale
4.92 out of 5 average rating, 128 reviews

5-Stars!! Cozy Home near the lake

Please answer our questions when requesting to book. If they are not answers, your request will be declined. Cozy home near the lake is a peaceful place to relax or adventure in the lakes region.The house is located right next to the Glendale Yacht Club and 0.3 miles or a 6 min walk (based on Google) to the Breeze Restaurant and water access at the Glendale Public Docks (no swim area). The house comes with a fully stocked kitchen, a grill, relatively fast internet and a 55" TV (no cable)

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
4.99 out of 5 average rating, 69 reviews

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.

Top guest favourite
The living area features a blend of comfortable seating, including a dark brown recliner and a soft sofa. A wooden coffee table is centrally placed, adorned with decorative items. Natural light illuminates the space, complemented by neutral walls and subtle décor.
Home in Lebanon
4.96 out of 5 average rating, 289 reviews

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Top guest favourite
A wide view captures the expansive landscape, showcasing frozen bodies of water and distant mountain ranges. The snow-covered ground is visible, along with patches of greenery and trees. A clear sky dominates above, highlighting the serenity of the winter scenery.
Home in Meredith
4.93 out of 5 average rating, 241 reviews

Fall/Ski Fun: Spacious Home near downtown Meredith

My place is close to Mills Falls in Meredith, close to skiing, casual and fine dining, art shops, wineries, art and antique shops, just minutes to 2 - 4 hour hikes with great views of White Mountains and Lake Winnepesaukee, a beautiful Association Beach, and family-friendly activities. You’ll love my place because of the comfy bed, the kitchen, the high ceilings, its cleanliness, and coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Top guest favourite
A vibrant sunset unfolds across the horizon, showcasing a gradient of orange, pink, and purple hues against a backdrop of silhouette trees and distant hills. Snow covers much of the ground, reflecting the colors of the sky.
Home in Wakefield
4.96 out of 5 average rating, 107 reviews

Cozy Retreat-NEW Coffee Bar

Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

Top guest favourite
The exterior of the cabin is framed by tall trees, showcasing a wooden facade and a covered porch. Two rocking chairs are positioned on the porch, while a large boulder and log stumps are visible in the grassy yard.
Home in Thornton
4.94 out of 5 average rating, 540 reviews

The Niche...crafted & forged

Welcome to the Niche, crafted and forged to preserve your memories. The many custom touches in this space echo our wish for your experience here: beautiful, unique, and unforgettable. As you relax, in a private wooded setting, we hope you find the peaceful time away you're searching for. The Niche is a cozy return after your day of swimming, hiking, skiing, or other recreational fun here in the White Mountains. You’ll have no shortage of activities to occupy your stay.

Top guest favourite
A spacious mountain retreat is framed by lush greenery and gardens, featuring multiple balconies and a large deck. It is positioned on a hillside, with stone walls and a manicured lawn leading up to the entrance. Woodlands provide a natural backdrop.
Home in Bristol
5 out of 5 average rating, 105 reviews

Newfound New Hampshire's Diamond on a Hilltop

This diamond on a hilltop is nestled on a mountain side in Bristol, NH over looking Newfound Lake w/ Cardigan Mtn. in the back drop. Newfound Lake Assoc. boasts of its reputation as one of the cleanest lakes in the world. Enjoy breathtaking views during the day & magnificent sunsets in the evening. The colorful gardens are surrounded by woodlands. Relax to the sound of the babbling brook. This peaceful place beckons you to slow your pace & nourish your soul.

Popular amenities for house rentals in Wolfeboro

When is the best time to visit Wolfeboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$379 SGD$388 SGD$385 SGD$390 SGD$402 SGD$488 SGD$493 SGD$493 SGD$441 SGD$454 SGD$429 SGD$455 SGD
Avg. temp-5°C-4°C1°C7°C14°C19°C22°C21°C16°C10°C4°C-2°C

Quick stats about house rentals in Wolfeboro

  • Total holiday rentals

    Explore 90 holiday rentals in Wolfeboro

  • Nightly prices starting at

    Wolfeboro holiday rentals start at $104 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,990 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 of Wolfeboro holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wolfeboro rentals

  • 4.9 Average rating

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