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Wolfeboro vacation rentals

Vacation rentals in Wolfeboro by owner — compare homes, condos and cabins, message verified hosts and book direct. See every charge before you pay.

Wolfeboro is known for its historic 19th-century charm, Lake Winnipesaukee, Brewster Beach, and the New Hampshire Boat Museum. Visitors enjoy outdoor activities like lake cruising, antique boating, and exploring the woodland trails of Wentworth State Park. Houfy connects travelers directly with local hosts, ensuring your vacation budget stretches further. Discover lakefront homes, charming New England cottages, and apartments with easy access to Alton Bay and Tuftonboro. Late spring offers the best time for tranquil boat rides and local festivals.

Top-Rated Vacation Homes in Wolfeboro

Browse the highest rated vacation properties in Wolfeboro.

Luxury Lakehouse, Sunset, Cen. Air & Private Dock

4 bd·3 ba
5· 46

$3,047.75 USD total for 3 nights

Nov 15 – 18, 2026

Peaceful lakeside retreat
The location of Rust Pond was wonderful because we were close to our golf course and to Wolfeboro for shopping and food. The lake was so quiet and peaceful. Glancing out the living room window to see an eagle perched on a branch on one of the trees was surely a treat! The home was lovely and in impeccable condition. The owners were very responsive and so easy to deal with. We will definitely return!
Stay August 2025

20 Mile Bay - Lake Winnipesaukee

4 bd·2½ ba
5· 126

$1,241.41 USD total for 3 nights

Nov 15 – 18, 2026

We are already planning our next visit! This was a perfect spot for our snowy weekend getaway. While I'm sure there's plenty to do in the surrounding towns we just wanted to hunker down and cook, watch movies, talk, and play games and this place had everything we needed. The house is in a great spot set back in the woods so it feels quite private. It's spacious enough so that everyone was comfortable, but also felt very cozy. Plenty of games and entertainment on site, and probably the best stocked kitchen I've experienced at an AirBnb in terms of appliances, cookware, utensils, etc. The hosts were super responsive and accommodating and made check-in, check-out, and the whole stay totally hassle-free. Truly a great find right on the lake.
J. · Stay January 2024

Lakefront Retreat w/ Hot Tub| Views| Dock| Kayaks

4 bd·2 ba
5· 13

$1,339.25 USD $1,225.33 USD total for 3 nights

Nov 15 – 18, 2026

This place is beyond 5 stars. The view is breathtaking taking, especially in the fall! We had our family come from other states to have a small reunion. It was perfect spacing for 7 Adults, 1 child and Two dogs. There was enough seating for all of us to have our meals together ❤️ We took walks together through the trails that are available next to the house. Took the paddle boat out and the view is amazing on the water. My 3 yr old Granddaughter even tried a little fishing. She just likes to put the worms on the hook. The hot tub is a great way to relax after dinner. Sherre is a terrific host!!! 10 stars! Any questions we had she was right there to answer them. We had the back light go out and she was there in 15 min to fix it with her ladder. You will not be disappointed with your stay even if it rains all day. Enjoy and hope you make great memories like our family did!
H. · Stay October 2025

Cottage 12 - 1 Bedroom Wolfeboro Winnipesaukee

1 bd·1 ba
5· 93

$621.62 USD total for 3 nights

Nov 15 – 18, 2026

Cabin was beautiful! Very clean, well equipped. Comfortable enough bed and area is great. My only issue was cabin #12, where I stayed, was not a single family building. I was under the impression that it was when booking it. There was actually another unit next door that I shared a wall with, and those people were NOISY, all night, the entire 5 days I stayed. Not a fault of the property, maybe I should have read the ad better but that was frustrating as I was actually here for work, not pleasure and was kept up all night by a very thin shared wall. The rest of the place was perfect. Very clean, very well thought out, good water pressure and soft sheets. Would absolutely stay again, just probably in one of the single occupancy buildings. Only other issue I had was very very minor. I was texted a code to get in, but it was probably a typo because the code was wrong. I was able to look through my email and find the right one very quickly though. Thank you so much for your hospitality!!!
M. · Stay September 2026

Cottage 4 - 1 Bedroom Wolfeboro Winnipesaukee

1 bd·1 ba
5· 84

$602.05 USD total for 3 nights

Nov 15 – 18, 2026

We had a great stay at The Cottages for a family wedding in the area. We had all the necessary items, space, and (most of all) hot water for all the required showers and primping for the event! The space was a little smaller and a little further from the water than I had pictured in my mind, but I don't think it was the fault of the description. I just had something else pictured. Dunkin, diner, pizza, grocery, and convenience store were all within easy walking distance. We didn't dine in Wolfeborough during our stay but the location of The Cottages looked to be convenient to a number of different places. Also, we blew a fuse while we were getting ready and Brian was immediately dispatched to help us. We had complete power very shortly after losing it. We will definitely stay at The Cottages again when we are back in the area visiting family!
A. · Stay June 2023

Main House - Wolfeboro - Winnipesaukee

5 bd·3 ba
5· 70

$1,742.16 USD total for 3 nights

Nov 15 – 18, 2026

This was a wonderful location for our long weekend. I recently booked this property in Wolfeboro as part of a long weekend spent doing outdoor activities in the surrounding area - paintball in Center Barnstead and skeet shooting in Ossipee. A large group of us attended - 11 adults - and the property was easily able to fit all of us. The best part was that there was a bed for everyone, which is a difficult perk to find. The property was very clean and open, with a fully stocked and functional kitchen as well as lovely outdoor space with working gas grill. Melissa was a great host and responsive to all of my questions and requests. The entire trip was almost seamless from a logistical standpoint, and I cannot thank Melissa enough for helping to achieve this result. I will definitely look up this property if I am ever planning a group outing in New Hampshire in the future. I fully recommend this location. Thank you, Melissa!!
G. · Stay May 2023

$650.99 USD total for 3 nights

Nov 16 – 19, 2026

Cottage 7 - 1 Bedroom Wolfeboro Winnipesaukee

1 bd·1 ba
5· 2

$587.37 USD total for 3 nights

Nov 15 – 18, 2026

Wonderful stay at Cottages at Wolfeboro.
I will say right up front that I am picky about accommodations. We were in Wolfeboro for a reunion dinner at the Wolfetrap Grille and needed a place to stay for just one night. We were more than satisfied with the attention we received upon booking Cottage 7 and the cottage itself was a delight. Well appointed and immaculate, it was a pleasure staying there. I have already recommended it to friends who will be in the area and we will definitely be back again. Thank you, Melissa and Robin.
C. · Stay August 2025

Recommended Homes in Wolfeboro

Handpicked properties we think you'll love in Wolfeboro.

Cottage on High

2 bd·1 ba
4.87· 38

$1,708.88 USD total for 3 nights

Nov 15 – 18, 2026

Cottage 11 - 1 Bedroom Wolfeboro Winnipesaukee

1 bd·1 ba
4.85· 46

$549.06 USD total for 3 nights

Nov 15 – 18, 2026

Cottage 5-6 - 2 Bedroom / 1 Bath

2 bd·1 ba
4.9· 39

$1,320.86 USD total for 3 nights

Jan 2 – 5, 2027

$1,100.00 USD $1,010.00 USD total for 3 nights

May 9 – 12, 2027

$598.72 USD total for 3 nights

May 2 – 5, 2027

$824.29 USD total for 3 nights

Nov 25 – 28, 2026

$523.52 USD total for 3 nights

Nov 15 – 18, 2026

$1,013.20 USD total for 3 nights

Nov 15 – 18, 2026

Why visit Wolfeboro

Discover what makes Wolfeboro a perfect vacation rental destination.

Explore Lake Winnipesaukee

Enjoy activities on NH's largest lake

Take a boat tour or go fishing on Lake Winnipesaukee, just a mile from downtown Wolfeboro. It's a haven for water enthusiasts.

Visit Wright Museum

Delve into WWII history

The Wright Museum is only 0.5 miles from downtown and offers unique exhibitions on American experiences during WWII.

Hike Cotton Valley

Scenic trails for all levels

The Cotton Valley Rail Trail is an easy 12-mile trail starting near Wolfeboro, ideal for hiking and biking through picturesque landscapes.

Dine at Wolfetrap Grill

Savor fresh local seafood

Located 2 miles from the city center, the Wolfetrap Grill & Rawbar offers delightful seafood dishes in a casual setting with lake views.

Where to stay in Wolfeboro

The best areas and neighborhoods for your vacation rental in Wolfeboro.

Downtown Wolfeboro

A charming area with boutiques, cafes, and the scenic Back Bay. Perfect for shopping and dining, all within walking distance.

Best for: shopping, culture, dining

Wolfeboro Falls

Just north of downtown, this area is known for its close proximity to hiking trails and natural beauty, perfect for outdoor lovers.

Best for: nature, hiking, families

South Main Street

A residential area offering lakeside access and peaceful surroundings, ideal for those looking for tranquility and scenic views.

Best for: relaxation, lakeside access

Mirror Lake

A serene neighborhood with direct access to Mirror Lake, offering a quiet retreat and opportunities for paddling and fishing.

Best for: water activities, solitude, fishing

Find Wolfeboro vacation rentals that suit your style

Vacation homes and more — pick the kind of Wolfeboro vacation rental you want, then book it direct with the host.

Wolfeboro vacation rentals with free WiFi, hot tub or air conditioning

Free WiFi, hot tub, air conditioning and more — every Wolfeboro vacation rental here is listed by a verified host and bookable direct, with the price the host set.

Top attractions in Wolfeboro

All within driving distance of Wolfeboro vacation rentals.

Wright Museum of World War II

Learn about America's Home Front during WWII with interactive exhibits. · 0.5 miles

Cate Park

A lakeside park in downtown Wolfeboro where you can enjoy free summer concerts. · 0.2 miles

Clark House Museum Complex

Discover Wolfeboro's history in this collection of historic buildings. · 0.9 miles

Wolfeboro Town Docks

Rent a kayak or go for a scenic boat ride on Lake Winnipesaukee. · 0.3 miles

Abenaki Ski Area

Family-friendly skiing and snowboarding just a short drive away. · 2 miles

Great Waters Music Festival

Catch live performances each summer with views of the lake. · 1 mile

Getting to and around Wolfeboro

Wolfeboro is best navigated by car, with nearby airports facilitating access.

Nearby Airports
MANCHESTER-BOSTON REGIONAL AIRPORT
Located about 55 miles southwest of Wolfeboro, offering numerous domestic flights.
PORTLAND INTERNATIONAL JETPORT
Approximately 65 miles to the east, with flights to major U.S. cities.
Driving
RENTAL CARS
Available at nearby airports and in town for exploring the Lakes Region at your own pace.

Similar vacation rentals near Wolfeboro

Homes within 60 miles of Wolfeboro, from verified hosts.

Spacious 5BR Retreat Near Cranmore | Sleeps 14 |

5 bd·3 ba
4.86· 185

$1,864.25 USD total for 3 nights

Nov 15 – 18, 2026

Lake & Mountain View Retreat|Near Gunstock & Winni

4 bd·3½ ba
5· 114

$2,859.87 USD total for 3 nights

Nov 15 – 18, 2026

Sleeps 13 in North Conway w Game Room and Pool

5 bd·3 ba
4.96· 24

$1,908.88 USD total for 3 nights

Nov 15 – 18, 2026

Lake House on Belleau Lake; Hot Tub, Kayaks!

4 bd·2 ba
5· 234

$1,381.30 USD total for 3 nights

Nov 15 – 18, 2026

Townhouse at Atty Mountain Village, walk to skiing

3 bd·2 ba
4.88· 59

$1,139.25 USD total for 3 nights

Apr 12 – 15, 2027

Oceanfront Penthouse Salisbury

5 bd·2 ba
5· 196

$1,041.00 USD total for 3 nights

Nov 15 – 18, 2026

Good Friday Chalet | Walk to Village + Cranmore Mt

3 bd·2 ba
5· 168

$919.17 USD total for 3 nights

Nov 15 – 18, 2026

Ammonoosuc House, cozy cabin - no cleaning fee!

2 bd·1 ba
4.93· 631

$439.43 USD total for 3 nights

Nov 15 – 18, 2026

Sunday Slopes | Game Room + Snowmobile Trails

5 bd·3 ba
4.93· 103

$1,178.15 USD total for 3 nights

Nov 16 – 19, 2026

The SeaTurtle @ Ashworth Place

2 bd·1½ ba
5· 42

$1,454.73 USD total for 3 nights

Nov 15 – 18, 2026

Peaks Islnd Seaside Cottage hot tub/decks/walkable

3 bd·2½ ba
4.9· 48

$1,314.65 USD total for 3 nights

Nov 15 – 18, 2026

North Country Lake House - Loon

1 bd·1 ba
5· 413

$330.38 USD total for 3 nights

Nov 15 – 18, 2026

Explore near Wolfeboro

Cities and towns within driving distance of Wolfeboro, each bookable direct with the host.

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