Holiday rentals in Wolfeboro

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Top-rated holiday rentals in Wolfeboro

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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
4.99 out of 5 average rating, 78 reviews

King’s Cottage PERFECTLY LOCATED!

Welcome to our newly updated 3bd/1ba cottage, where there is a lot to do or nothing to do at all! The cottage offers the perfect getaway for couples or small family. First floor living with 2 additional bedrooms upstairs, plus tween/teen lounge area & kids corner. The cottage is on a quiet street, but walkable to coffee, restaurants, and downtown shopping. Great proximity to Lake Winni, Sewall Woods, Cottonwood Rail Trail. It's an easy 1 hr drive from Manchester airport or 2 hr from Boston.

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, 27 reviews

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

Guest favourite
Home in Wolfeboro
4.83 out of 5 average rating, 12 reviews

Gram's House

You will enjoy easy access to everything from this historic home. Town is 0.4 miles away. Hang out on the deck overlooking Wolfeboro Bay. Enjoy a swim whenever you want. And there are spring, fall, and winter activities in the area! You will have use of a private beach, a raft, canoe, kayaks, and beach toys (but no dock). Hiking and ski trails are within a short walk or drive. Great gathering place - our family has enjoyed many special events here and you will too! Includes a two car garage.

Top guest favourite
Guest house in Alton
4.97 out of 5 average rating, 308 reviews

Vineyard Terrace - Modern & Beautiful

Step into a secluded vineyard retreat where elegance and breathtaking scenery meet. This suite offers a king bed, modern comforts, and a spacious patio pergola with sweeping vineyard and mountain views. Enjoy a well-equipped kitchen, dining and living area, or unwind in the new shared hot tub — perfect for romantic getaways or extended stays. Though other guests share the property, this space is yours to enjoy. 5 min to Lake Winni, 20 min to Wolfeboro, 25 min to Gunstock & Bank of NH Pavilion.

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
4.87 out of 5 average rating, 184 reviews

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!

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, 71 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
A sleek black stove is set against a rustic brick wall, featuring a glowing flame that provides warmth. In the foreground, softly blurred decorative ornaments hint at a holiday theme, while a patterned rug adds comfort to the inviting space.
Cottage in Wolfeboro
4.96 out of 5 average rating, 130 reviews

Lake Winnie Cozy Cottage Getaway

Welcome to Lake a Dream… your spot 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 from the property 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 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.
Guest house in Wolfeboro
4.97 out of 5 average rating, 68 reviews

Maple Hill 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.

Guest favourite
Flat in Wolfeboro
4.86 out of 5 average rating, 94 reviews

Back Bay Tuck-Away *Private Downtown Parking Spot!

** Brand new Puffy Mattress - Awarded Best Luxury Mattress of 2023 ** Bring your favorite person on a romantic, stylish, private getaway. Centrally located in Downtown Wolfeboro, NH, The Oldest Summer Resort in America. Private keypad access, free private parking, directly outside your door, on the back side of Main Street, right in the heart of town. Ten steps to the side walk on North Main Street and a two minute stroll down to Back Bay Winnipesaukee docks.

Top guest favourite
The living room showcases a spacious layout with a warm-toned leather sofa and a circular coffee table. A stone fireplace serves as a focal point, complemented by plants and cozy seating arrangements. Natural light filters through windows, enhancing the inviting ambiance.
Home in Wolfeboro
4.99 out of 5 average rating, 68 reviews

Relaxing hidden gem in Wolfeboro

Located within just 7 minutes from Lake Winnipesaukee, Wolfeboro Center, Allen Albee Beach, and Lake Wentworth, Beach Pond Acres is your perfect year round vacation resting place. Indulge in the abundance of activities in the nation’s oldest summer resort, including fishing, water sports, and relaxing lake beaches and Gunstock Ski Resort. Enjoy the privacy of an open, cozy, and light filled home, sitting on five acres of abundant wildlife and vivid greenery.

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
4.94 out of 5 average rating, 18 reviews

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.

Top guest favourite
A historic Victorian house features a multi-toned exterior with a distinctive turret. Multiple decks provide seating areas, while the well-maintained grounds include white picnic tables and colorful landscaping. Large windows offer views of the surrounding area, creating a welcoming presence at the waterfront.
Apartment in Wolfeboro
4.98 out of 5 average rating, 240 reviews

Elegant condo on the water in downtown Wolfeboro!

**WINTER SPECIAL** Stay Friday and Saturday and Sunday night is free on non-holiday weekends. Often described as Wolfeboro's favorite house, this historic Victorian sits right downtown Wolfeboro and on the water looking across to the town docks, Brewster Academy and Wolfeboro Bay. This two-story unit, occupying the second and third floors, has a beautiful porch overlooking the bay and is located by the famous Yum Yum Shop.

Popular amenities for Wolfeboro holiday rentals

When is the best time to visit Wolfeboro?

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Avg. price£127£130£131£132£165£188£207£203£174£174£170£162
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Wolfeboro?

    Four-legged friends are welcome in Wolfeboro. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Wolfeboro?

    Yes! Work meets play with ease at over 80 vacation rentals in Wolfeboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly cottage rentals in Wolfeboro?

    Wolfeboro has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in guesthouse rentals in Wolfeboro?

    Experience the best of Wolfeboro with our guesthouse rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Wolfeboro have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Wolfeboro. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Wolfeboro have a bbq area?

    Absolutely! We offer over 20 cottage rentals with a bbq area in Wolfeboro. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wolfeboro have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Wolfeboro. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cottage Rentals in Wolfeboro?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 20 homes with a bbq area, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Wolfeboro

  • Total holiday rentals

    Explore 220 holiday rentals in Wolfeboro

  • Nightly prices starting at

    Wolfeboro holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 7,450 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    210 of Wolfeboro holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Lake access, Gym and BBQ grill across Wolfeboro rentals

  • 4.9 Average rating

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