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Vacation rentals with a kayak in Wolfeboro

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Top-rated kayak rentals in Wolfeboro

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

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Cabin in Bradford

5 out of 5 average rating, 4 reviews

Little Red Wing 50s Lake Cabin

Cozy 1950's waterfront cottage on Lake Massasecum! In the Winter - Skiing is close by. Snowmobiling, Ice Fishing, and Cross County Skiing are allowed on the lake. It’s very important to test the ice for safety. In the Summer - Power boats are allowed on Lake Massasecum and it is also the perfect place for canoes, kayaks, great fishing and bird watching! Three kayaks, one canoe, and one paddle board are available for use with cabin rental. Also comes with the use of a private swim platform.

Home in Shapleigh

4.98 out of 5 average rating, 127 reviews

Secluded Lakehouse/2 private docks*Hottub*big yard

Bring your family or friends for a fun and relaxing stay on Mousam Lake this summer! With 3 bedrooms, and additional loft and a basement sleeping area, there's room for everyone! Explore the lake with canoes, kayaks and paddleboards available to you or bring your own boat, the public boat launch is across from our front dock! When you are not enjoying the lake, the house provides many spaces for your favorite yard games, a screen house to play cards or have a drink and unwind in large hot tub!

Home in Henniker

4.75 out of 5 average rating, 176 reviews

Year-round Water Views ,cozy house near ski resort

Look no further than our waterfront house in Henniker, NH! With a full kitchen, 2 bedrooms, and a large living/dining area with a panoramic view of the pond, you'll have everything you need to relax and unwind. And with pond access just a few steps away, you can easily enjoy activities like fishing, kayaking, and hiking. Want to explore the area? We're just minutes away from Pat's Peak Ski Area and the Contoocook river for white water kayaking. And don't forget to spend some time at Weirs Beach!

Home in Shapleigh

5 out of 5 average rating, 4 reviews

Lakefront Home with Sandy Beach! Kayaks, SUP, Peda

Welcome to The Lazy Loon on Square Pong! Wake up to the sounds of loons calling. This home is located on a large lot with about 100 ft of lake frontage. Square Pond is a spring fed body of water known for its sandy beaches, deep and clean waters, and great fishing! It is one of the largest lakes around, however very private due to no usable public boat launch. The expansive, sandy beach area offers a great space for games, grilling out, and relaxing. The large lakeside fireplace is a great spac

Cottage in Northwood

4.93 out of 5 average rating, 109 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Home in Middleton

4.96 out of 5 average rating, 136 reviews

Blue Breeze - Private lakefront w/ Hot Tub

This huge lakeside house is a great experience for all of your friends and family to enjoy all the New Hampshire lakes region has to offer. There is incredible nature all around! Some of our favorites nearby: 11min to a nearby brewery 12min to a great breakfast spot 14min to a farm stand and pick-your-own produce 17min to a nearby winery 21min to Hannafords grocery store 22min to Alton Bay 25min to Wolfeboro 29min to Mt. Major with views of Winnipesaukee 38min to Gunstock mountain for skiing

Cottage in Wolfeboro

4.89 out of 5 average rating, 76 reviews

🌟Winni Cottage beach, dock, kayaks, SUP & more! 🌈🍸

Great Wolfeboro Winnipesaukee waterfront cottage on Back Bay Wolfeboro. Includes 5 kayaks, 2 canoes, paddle board & row boat ! 3 bedrooms, indoor and outdoor hot showers! Large deck and big grassy lawn and camp fire! Min of 3 nights, weekly in summer. Lovely protected bay, great for novice paddlers. 40 ft dock, beach area. Swim platform, great for swimming to from dock. Bring your own boat or rent one! Walk to town in 5 mins, bring your bikes, great bike trails! Very relaxing quiet spot!

Cottage in Middleton

4.97 out of 5 average rating, 152 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.

Cottage in Parsonsfield

4.88 out of 5 average rating, 139 reviews

Riverpine Retreat - clean&bright waterfront home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Cabin in Harrison

4.99 out of 5 average rating, 121 reviews

Get away at Crystal Lake

Escape the lake region crowds on the calm water of Crystal Lake. Watch the sunset from the private waterfront/dock, kayak to take tour of the lake. Steps away from the center of Harrison and 2 boat launches, and only a short drive from downtown Bridgton. If you'd like a hike or bike instead, it's also a short drive to the mountains. Relax lakeside while your family enjoys the small beach, 2 kayaks, dock, or simply float about with a drink in hand. Note: waterfront across street

Home in Limerick

4.79 out of 5 average rating, 14 reviews

Sokokis Cottage Lakefront cottage w/ dock kayaks

Just 2 hours from Boston and 1 hour from Greater Portland, ME, Sokokis Lake is a fantastic ice fishing spot! Relax under our majestic willow tree with stunning lake views at every turn. During the warmer months, explore the lake in our 2 kayaks or launch your own boat from the public ramp neaby. Enjoy evenings by the fire pit while watching the sunset. Plus, a supermarket, ice cream, fried seafood, and pizza are just a short walk away. Your lakeside escape awaits!

Cottage in Middleton

4.96 out of 5 average rating, 164 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Wolfeboro kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Northwood

4.94 out of 5 average rating, 17 reviews

Lakeside cabin w/ beach & dock

Home in Wakefield

5 out of 5 average rating, 17 reviews

In the Trees - NH w/ Lake Access

Home in Sanbornton

4.95 out of 5 average rating, 37 reviews

Dog, Boat Friendly Waterfront home- no Airbnb fees

Home in Laconia

4.93 out of 5 average rating, 231 reviews

The Riverhouse Kayaks Pool Table Firepit Downtown

Home in Barnstead

4.89 out of 5 average rating, 116 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

Home in Gilford

4.92 out of 5 average rating, 12 reviews

3BR/3BA Lake Winnipesaukee Waterfront Home w/ dock

Home in Wakefield

4.88 out of 5 average rating, 16 reviews

Lakefront Retreat! Dog Friendly!

Home in Danbury

4.98 out of 5 average rating, 49 reviews

Welcome to The Dam House!

Cottage rentals with a kayak

Cottage in Conway

4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

Cottage in Alton

4.98 out of 5 average rating, 115 reviews

“Stay Awhile in the Lake's Region”

Cottage in Thornton

4.94 out of 5 average rating, 145 reviews

Cottage with antique charm view & river HSI Wi-Fi

Cottage in Laconia

4.94 out of 5 average rating, 110 reviews

Completely updated detached cottage/Paugus Bay!

Cottage in Conway

4.95 out of 5 average rating, 318 reviews

20ft from the Water with Mountain View!

Cottage in Gilmanton

4.96 out of 5 average rating, 112 reviews

Minutes to Gunstock MT - Family Lakeside Getaway

Cottage in Freedom

4.79 out of 5 average rating, 455 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Cottage in Newbury

4.95 out of 5 average rating, 214 reviews

Large Private Lake House

Cabin rentals with a kayak

Cabin in Andover

4.94 out of 5 average rating, 108 reviews

Little House on the Lake in the Forest

Cabin in Holderness

4.86 out of 5 average rating, 102 reviews

Beautiful private cabin on Big Squam Lake

Cabin in Barnstead

4.95 out of 5 average rating, 199 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

Cabin in Conway

4.96 out of 5 average rating, 126 reviews

The Conscious Cabin

Cabin in Waterford

4.94 out of 5 average rating, 158 reviews

Lakeside Cabin Nestled in the Pines

Cabin in Bridgton

4.93 out of 5 average rating, 111 reviews

Private cabin w hot tub,skiing,firepit & mountains

Cabin in Denmark

4.95 out of 5 average rating, 169 reviews

Maine Lakes-Pleasant Mt-Private Trails

Cabin in Wakefield

4.97 out of 5 average rating, 239 reviews

Beautiful Log Cabin on Belleau Lake -2900 sqft!

Quick stats about vacation rentals with a kayak in Wolfeboro

Total rentals
50 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore