Holiday rentals in Wolfeboro

4.98 out of 5 average rating, 241 reviews

Farm stay in Alton

Mountain View - Modern & Beautiful

Kick back and relax in this stylish apartment space, with its own entrance around the back of the home! Modern construction w/ a king bed, large outdoor patio space w/ mountain views. A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have a private space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

4.98 out of 5 average rating, 55 reviews

Guest house in Wolfeboro

Luxury Beachfront Cottage - Perfect summer getaway

Summer bliss in a restful lakeside cottage on pristine Lake Wentworth just a short jaunt from Wolfeboro. Quiet. Comfortable. Soothing. This premier destination is a serene 6 acre waterside refuge with expansive views and 5 star quality for those who appreciate attention to detail. Relax on the beach patio enjoying the firepit & sunset. Fill your days with kayaking, biking or nothing at all. Nap on the hammock. Cuddle up in a bed boasting luxury linens hand pressed just for you. . This is magic.

4.86 out of 5 average rating, 146 reviews

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!

4.98 out of 5 average rating, 153 reviews

Flat in Alton

Pretty & Peaceful….close to Lake Winni!

Welcome to your Alton Bay retreat! Come relax & make lasting memories. Very clean, well stocked full kitchen & bath. Across the street is 200 acres of picturesque hiking trails & fishing. Turn left at the end of driveway and enjoy a scenic walk along Winni. Quiet location but close enough to Lake Winnipesaukee, Mt Major, Wolfeboro, Bank of Pavillion, boat launches, & docks, beaches, restaurants, shopping, sking, snowmobiling, boat rides, scuba diving, biking, kayaking, leaf peeping!

4.89 out of 5 average rating, 19 reviews

Flat in Wolfeboro

Peaceful getaway with King Bed near Town

Welcome to the perfect Wolfeboro Getaway! King size memory foam mattress for a rejuvenating nights sleep. You will love the peace and quiet of this location with easy walkable access to everything in downtown Wolfeboro, Back Bay, and the waterfront. For nature lovers, there's hiking trails right at the end of the street, just take a left out the front door. Please note: There is a kitchenette with sink, refrigerator, coffee maker, toaster oven, and plug in cook top but no actual stove.

4.95 out of 5 average rating, 110 reviews

Cottage in Wolfeboro

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.

5 out of 5 average rating, 21 reviews

Guest house in Wolfeboro

Sugar Hill Cottage Suite

Come and enjoy a relaxing stay at Sugar 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.

4.95 out of 5 average rating, 21 reviews

Quaint Wolfeboro NH Home.

Quaint Wolfeboro NH Short-Term Rental - Centrally Located Welcome to our charming short-term rental in Wolfeboro, NH! Located just 5 minutes from downtown Wolfeboro, our cozy Cape home offers a perfect getaway for those looking to explore the beauty and amenities of this historic lakeside town. With its convenient location, you'll have easy access to great restaurants, shopping, walking trails, a public golf course, museums, Molly the Trolly, beaches, and lakeside activities.

5 out of 5 average rating, 87 reviews

Cabin in Wolfeboro

Sweet Apple Camp at Grey Shingles Camps

The Grey Shingles Camps property has been a cottage colony since the 1940's. After extensive renovations, our guests enjoy this historic property with a modern sensibility! The property has five acres of open lawn ,woodland, orchard, and private waterfront with sandy beach and docks on pristine Rust Pond. Amenities include kayaks, SUP's, canoes, sunfish; Pickleball, basketball, & more. The Rec Hall has a full kitchen, living room with cable TV, ping pong, foosball, & more!

4.96 out of 5 average rating, 139 reviews

Apartment 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.

4.85 out of 5 average rating, 82 reviews

Flat in Wolfeboro

Back Bay Tuckaway

** 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.

4.98 out of 5 average rating, 60 reviews

Cottage in Wolfeboro

Relaxing Retreat in Historic Schoolhouse

Enjoy an idyllic stay at this restful retreat on historic Cotton Mountain with stone walls and perennials is a 12-minute drive from Wolfeboro center with plenty of shops, restaurants, and things to do. This unique property, formerly an 1860 schoolhouse has been renovated to provide a place for a relaxing getaway, a girlfriends' celebrations, a small family gathering, or downtime from adventurous outdoor activities.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Wolfeboro holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Wolfeboro

4.96 out of 5 average rating, 23 reviews

Cozy Lake House in Wolfeboro, NH

AlRating, 5 stars3 weeks ago

Zack was very responsive throughout our experience. The house was very clean and spacious. The views were fantastic. We enjoyed the peddle boat on the water we wish the weather was nice enough to enjoy the paddle boards. It was a great quite getaway

4.94 out of 5 average rating, 34 reviews

Quaint Cottage Close to Lakes Dog Friendly

PhilipRating, 5 stars4 months ago

We've stayed at this location a couple times now and it's been perfect each time. Close to downtown Wolfeboro, clean, pet-friendly, and well-appointed.

5 out of 5 average rating, 5 reviews

Charming home in Wolfeboro

JuliaRating, 5 stars8 months ago

I can’t say enough wonderful things about our stay at Jessica’s beautiful New Hampshire home. She truly thought of everything to make guests feel welcome and comfortable, from the smallest details like toothpicks to the thoughtful touches of holiday candles. The house itself is absolutely gorgeous, and Jessica’s communication throughout our stay was prompt and incredibly helpful. I’m finding it hard to write this well-deserved review because I selfishly want to keep this hidden gem all to myself! If you’re lucky enough to book this place, you’ll be in for an unforgettable stay. Thank you, Jessica, for going above and beyond!

4.89 out of 5 average rating, 45 reviews

Win-win! Relax at our place & play at the lake!

JolitaRating, 5 stars8 months ago

Always happy when I stay here. Never had an issue with this listing or this host.

5 out of 5 average rating, 16 reviews

Bungalow in Wolfeboro

relax on crescent lake

AmyRating, 5 stars9 months ago

Incredible week! Not only are Kim & Nanci kind hosts, they’re kind souls. The pride they take in their gorgeous property is palpable. Just when I thought I couldn’t love Wolfeboro more or find it more charming, I discovered Kim & Nanci’s gem! Everything was perfect. Thanks for a magic stay!!

4.92 out of 5 average rating, 12 reviews

Cottage in Suissevale

The Nook at Ambrose Cove

ToriRating, 5 stars4 days ago

When we arrived at this small, lovely marina where the property is located, my first thought was: magical!!!!! Inside, a little oasis, modern and well appointed. A huge, comfy sofa, large TV, great bed and thoughtful amenities. We did not need the AC, but I tried it and it got cool, quickly. Outdoors: paddleboards, kayaks and a grill overlooking the lake and the homes along the lake. Stunning. It’s a less than a minute walk to the restrooms, which are also modern and pristine, and part of the experience. I genuinely loved our stay here! It’s a very special, private place in the best of ways. Highly recommend,

4.95 out of 5 average rating, 22 reviews

Cabin in Tuftonboro

Cardinals Nest - Lakeside Cottage In Winter Harbor

MaretteRating, 5 stars10 months ago

Loretta's cottage in Winter Harbor is absolutely lovely. A quick ride from Wolfeboro, it is in a great location if you are looking for peace and quiet. A wonderful way to unplug, and enjoy the lake. Loretta was a wonderful host, very communicative, and friendly. Would absolutely stay again!