Vacation rentals in Wolfeboro

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Top-rated vacation rentals in Wolfeboro

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

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Guest favourite

Farm stay in Alton

4.97 out of 5 average rating, 165 reviews

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

Nov. 11 – 18

$168 CAD per night

Guest favourite

Guest suite in Conway

4.99 out of 5 average rating, 420 reviews

Mountain View Studio

This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

May 20 – 25

$179 CAD per night

Guest favourite

Apartment in Tuftonboro

4.97 out of 5 average rating, 267 reviews

Apartment CenterTuftonboro minutes from Wolfeboro

This is a spacious lower- level apartment 1000 sq ft in our home . Our guests will have complete privacy with convenience parking . It features a large master bedroom and cozy second bed room. You have a large private kitchen , living room , a bathroom and laundry room . Our area offers many activities as well as shopping in historic down town Wolfeboro. A very short drive to all the best things that Lake Winnipesaukee offers. Please read all our description before booking . Thanks so much

Nov. 12 – 19

$216 CAD per night

Guest favourite

Loft in Barrington

4.96 out of 5 average rating, 490 reviews

Sunny, secluded studio loft apartment

Fully furnished studio apartment above home owners' garage with private entrance. Secluded 5.5 acre lot of land surrounded by beautiful woods. Vaulted ceilings with ladder to loft with queen bed. Big, sunny south-facing windows overlooking back yard and gardens. Homeowners are a laid-back, married gay couple, living in the main house with their 2 year old daughter and a dog. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

Oct. 24 – 31

$149 CAD per night

Guest favourite

Guesthouse in Belmont

4.99 out of 5 average rating, 200 reviews

Charming Pool/Garden Guest House

A little Paradise! Charming pool and guesthouse in country setting, birds and flowers galore. Much to do in the area, or just quiet, settling into some refresh-your-soul time. The guesthouse has all you need to feel at home. Within 15 minutes you'll find Gunstock Recreational Area, Highlands Mtn. Bike Park, Hermit Woods Winery, Funspot bowling and arcades, hiking, fishing, Shaker Village, Lakes Region Casino, NH Speedway, Bank of America Pavillion (concerts) and Tanger Outlet Shopping.

May 25 – Jun. 1

$205 CAD per night

Guest favourite

Apartment in Wakefield

5.0 out of 5 average rating, 56 reviews

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Nov. 28 – Dec. 5

$146 CAD per night

Guest favourite

Cottage in Middleton

4.96 out of 5 average rating, 136 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.

Dec. 9 – 16

$262 CAD per night

Guest favourite

Guesthouse in Wolfeboro

4.98 out of 5 average rating, 178 reviews

A charming loft Barn that sleeps 5.

Our 3000 sq ft renovated, rustic loft barn is located on 70 acres, very private, yet 2.5 miles from downtown Wolfeboro. Our barn sleeps 5, has full kitchen, bar, pool table, 65 inch TV and bath with shower. The barn has 1 double & 4 single beds, one set of single beds can be converted into a king upon request prior to stay. A perfect place to hang out with a few friends. Minimum age of primary renter 25. MAX 5 guests staying, please do not book if you have more. No parties.

Apr. 1 – 8

$531 CAD per night

Guest favourite

Apartment in Wolfeboro

5.0 out of 5 average rating, 17 reviews

Sunny 2 bedroom rental in Wolfeboro, New Hampshire

Sunny first floor two bedroom unit with wrap around porch and outside grill and seating. Unit is across street from Cotton Valley Rail Trail for walking to town and around the shore of Lake Wentworth. Walk across street to bike, walk or run the trail for miles. Also across street from public access to Lake Wentworth to launch your boats, canoes or kayaks. TV in each bedroom and the living room with Netflix, Hulu, Breezeline and Prime. Internet access at 1 gb speed.

Oct. 20 – 27

$266 CAD per night

Guest favourite

Guest suite in Meredith

4.9 out of 5 average rating, 234 reviews

Downtown! Studio w 3/4 Bathroom. Private Entrance!

This is one room with a queen bed and a 3/4 bathroom. Breakfast nook, mini-fridge, microwave, coffee maker. This room comes with it's own seperate entrance, private bathroom, and private patio (Patio is not open in the winter). Also we have off street parking for one or two cars. I am new to hosting, so for now please a two person max. Walking distance to downtown. Less than 100 yards and you are in the middle of downtown Meredith.

Sep. 26 – Oct. 3

$131 CAD per night

Guest favourite

Condo in Wolfeboro

4.97 out of 5 average rating, 188 reviews

Elegant condo on the water in downtown Wolfeboro!

** March & April special; stay Friday and Saturday night and get Sunday night for free** 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.

Nov. 14 – 21

$472 CAD per night

Guest favourite

Guest suite in Wolfeboro

4.83 out of 5 average rating, 99 reviews

Downtown, Cozy, Cute, and Convenient!

Walk just one block to the heart of downtown Wolfeboro, the "Oldest Summer Resort in America". Dine, shop, or just relax in the park overlooking the docks on Wolfeboro Bay. Walk to Mt Washington Ferry for a Lake Winnipesaukee ride or walk the Wolfeboro Rail Trail. You can take the Trolley or walk ten minutes to Brewster Beach. Also, there’s a playground steps away at the elementary school for the little ones.

Apr. 7 – 14

$168 CAD per night