Vacation rentals with a kayak in Lake Winnisquam

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Lake Winnisquam

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

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Guest favorite

Cabin in Bradford

5 out of 5 average rating, 5 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.

Guest favorite

Cottage in Wolfeboro

4.89 out of 5 average rating, 76 reviews

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

Great waterfront cottage on Wolfeboro’s Back Bay! Includes 5 kayaks, 2 canoes, a paddleboard & rowboat. 3 bedrooms, plus indoor & outdoor hot showers. Large deck, big grassy lawn, and cozy campfire area. Calm, protected bay—perfect for beginner paddlers. 40-ft dock, beach area, & swim platform on a mooring. Bring your boat or rent one to access main lake under the bridge. Just an 8-minute walk to town! Bring bikes explore scenic trails. A peaceful, relaxing retreat with all the lakefront fun.

Guest favorite

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

Guest favorite

Home in Middleton

4.94 out of 5 average rating, 162 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

Superhost

Home in Barnstead

4.84 out of 5 average rating, 101 reviews

Locke Lake Waterfront Escape

Completely renovated home with private beach and waterfront. The water drops off gently making it great for young children. Variety of rafts, beach toys, kayaks, paddle boards, pedal and row boat available for use. Great fishing in the summer, and ice fishing in the winter. Outdoor deck is wonderful for entertaining. Seasonal game room in garage with shuffleboard and more. Located about 15 mins south of Lake Winnipesaukee and 30 mins from Gunstock Mountain. *Linens and Towels now included!*

Superhost

Home in Wakefield

4.82 out of 5 average rating, 87 reviews

Pine River Pond

Directly on Pine River Pond, this 5-mile long, 570 acre lake has crystal clear water. This vacation rental is close to all of the area's most popular activities and ensures a memorable time! Swim in the summer, ice fish in the winter, numerous snowmobile trails or just get away from it all.This 1-bath property offers enough space to comfortably accommodate up to 10 guests, making it ideal for a family or group of close friends looking for an unforgettable New Hampshire lakeside retreat.

Top guest favorite

Cottage in Middleton

4.97 out of 5 average rating, 151 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.

Superhost

Cottage in Parsonsfield

4.88 out of 5 average rating, 155 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.

Guest favorite

Cabin in Andover

4.95 out of 5 average rating, 113 reviews

Little House on the Lake in the Forest

***7-night minimum in warmer months, Saturday check in/out*** Wake up to the call of loons in this tiny and cozy lakefront cabin. Nestled at the remote base of Mt. Kearsarge, with unobstructed views of Ragged Mountain, this location affords year-round adventure on the protected south shore of Bradley Lake. Five minutes from Proctor Academy, 90 minutes from Boston. This retreat mixes ample amenities and high-speed internet with outdoor adventure!

Guest favorite

Cottage in Middleton

4.96 out of 5 average rating, 182 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!

Guest favorite

Cabin in Grafton

4.87 out of 5 average rating, 218 reviews

Beautiful Serene Lake/Ski House with central AC

Come enjoy the summer at our beautiful secluded lake house in New Hampshire! Swim, fish, kayak right in our backyard! Enjoy a good night with friends and family sitting around the fire, roasting marshmallows and watching the beautiful stars or play some games inside our rustic cottage. Activities in the area include Newfound lake, hiking, golf, winery, NH rail trail, entertainment complex. Sheets, towels and other necessities provided.

Top guest favorite

Cottage in Middleton

4.99 out of 5 average rating, 101 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

A lovely lake-front cottage with a private beach on quaint Sunrise Lake! The house has a great view overlooking the water. Enjoy a beautiful morning view of the sun rising onto the lake with a cup of coffee or tea, grilling a tasty dinner on the deck, and toasting marshmallows in the fire pit for dessert. We also provide a double kayak so you can explore the mile-long lake from the easy launch point in front of the house.

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What guests are saying

Hidden Gem: Amazing lake house + all the amenities

5 out of 5 average rating, 38 reviews6 months ago

My friends and I are photographers who make an annual fall getaway. Mike's place was beyond what we hoped for! It started with great communication--Mike answered any and all questions very quickly and offered additional suggestions of places to go and things to do. The house was located way off the beaten path on a very private road, right on a large pond. The scenery was gorgeous and we didn't really even have to leave the property to find beauty! We really enjoyed relaxing on the porch with it's fire table in the evening! Hopkinton is a beautiful small town that we enjoyed exploring! We hated to leave, but all of us look forward to booking this amazing place again very soon!

Cabin in Hopkinton

What guests are saying

Best View on Lake Winnipesaukee! Bear Island!

4.88 out of 5 average rating, 24 reviews6 months ago

We had an amazing time at the cabin. The sunrises were gorgeous, cooking on the grill, kayaking/paddle boarding, cozy fires, and everything we could have needed! We made such great memories and appreciated you and Matt’s hospitality so much. The cabin was great and so were you guys. We will definitely be back!

Island in Meredith

What guests are saying

Bow Lake Family Getaway

5 out of 5 average rating, 8 reviews6 months ago

My friends & I stayed at Cindy’s place for a wedding weekend. It was a beautiful lake house & perfectly accommodated us. We enjoyed the spacious living room & game room & cooked breakfasts in the kitchen. Cindy was quick to reply with any issues & even helped bring an item of clothing that was left to us! We all agreed that we’d come back again during warmer months to get use out of the kayaks & other lake amenities! Thanks again, Cindy!

Home in Strafford

What guests are saying

Remodeled Waterfront Home - Private Dock/AC/Kayaks

5 out of 5 average rating, 12 reviews1 week ago

The house is beautiful and comfortable. The kitchen is fully stocked with anything you'd need, and the laundry works very well. I thought the beds were also quite comfortable. My favorite part of the house was the porch overlooking the water, which was very peaceful, and the very easy to use fireplace that added a lot of warmth and coziness.

Home in Belmont

What guests are saying

Lakeside Lodge - a waterfront home on Lake Winona

4.9 out of 5 average rating, 48 reviews6 months ago

We were two couples and enjoyed our stay at the lodge. It is well organized and located in a beautiful setup on the lake. A relatively short 30 minutes drive allowed us easy access to the white Mountains attractions. Vanessa was proactive on closing the open space above the bedroom doors just before we came - so this issue as reported in some other reviews has gone away… in short - highly recommended!

Home in New Hampton

What guests are saying

Dog, Boat Friendly Waterfront home- no Airbnb fees

4.95 out of 5 average rating, 37 reviews8 months ago

This is an incredibly comfortable and remarkably well equipped lakefront house. Plenty of kitchen supplies and tools to keep the cooks happy, and all of the water gear anyone could ask for. We especially appreciated the large porch overlooking the lake. Close to the busy road (as was described in the listing), but blocked off and made visually private by fencing. Owners incredible, responding almost instantly, warmly, and generously.

Home in Sanbornton