Vacation rentals with a kayak in Wakefield

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Top-rated kayak rentals in Wakefield

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

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Guest favorite
The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.
Home in Naples
4.99 out of 5 average rating, 159 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Top guest favorite
The open-concept living area features a sleek gray sofa with decorative pillows and a spacious wooden dining table. Natural light floods the room through large windows, while a wall-mounted TV enhances the entertainment options. The warm wooden ceiling adds a cozy touch.
Cottage in Wakefield
4.99 out of 5 average rating, 103 reviews

Gorgeous Romantic Lakefront Getaway

Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford
4.9 out of 5 average rating, 555 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Top guest favorite
Home in Wakefield
4.97 out of 5 average rating, 101 reviews

Getaway to the Lake. Just 30’ from the water.

Step out of the house and onto to a beautiful deck. From the deck to the water is just 30 feet of sandy beach! Located right on Pine River Pond, this 5-mile, 570 acre lake has crystal clear water. The gently sloping property makes it ideal for multi-generational families. Swim in the summer, ice fish in the winter or just get away from it all in the fabulous peace and quiet of New Hampshire. Best fall foliage in New Hampshire can be found right on Pine River Pond and the adjacent roadways.

Top guest favorite
Cottage in Buxton
4.97 out of 5 average rating, 160 reviews

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Off-Season Escape Nestled just next door to Ferris Farm, our family-run flower farm, this charming cottage offers the perfect private space to rest and recharge. Even as the gardens rest for winter, there’s beauty all around. Stay in and enjoy slow, coffee-filled mornings, quiet walks around the property, and cozy, starlit evenings by the fire pit. Or take a drive and explore Portland’s diverse food scene. Perfect for a romantic retreat, solo escape, or remote work getaway.

Top guest favorite
The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.
Apartment in Wakefield
4.98 out of 5 average rating, 108 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.

Guest favorite
A red post and beam house is nestled among trees, featuring multiple windows and a sloped roof. A wooden deck extends from the entrance, leading to a gently sloping yard surrounded by lush greenery. Sunlight filters through the leaves overhead.
Home in Limerick
4.93 out of 5 average rating, 134 reviews

Lakefront Getaway

Looking for a quiet peaceful getaway? Our Maine post and beam home is set on 7 acres of lake front. Great getaway to enjoy marshmallows and a roaring fire, kayaking, canoeing, swimming, boating or enjoy a great movie. For downhill skiers proximity to King Pine, Sunday River, Shawnee Peak and Black Mountain. Cross country and snow shoeing on property and on the lake. If you have a snow mobile- great trails available. Finally, great shopping in nearby North Conway at the outlets.

Top guest favorite
A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.
Cottage in Middleton
4.97 out of 5 average rating, 167 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.

Guest favorite
The exterior of the custom-built home is surrounded by tall trees, showcasing a wooden structure with a sloped roof and large windows. A deck features a built-in railing and a shaded pergola, while a set of stairs leads down from the entrance.
Home in Wakefield
4.93 out of 5 average rating, 121 reviews

Spacious Belleau Lake House Amongst the Trees

You and your family & friends will feel right at home in this spacious custom built home in the tall trees across the street from beautiful Belleau Lake. There are three levels of living space, making it a great destination for small or mid sized groups or families looking to share a vacation without compromising privacy. It is also perfectly cozy for a couple. Enjoy the peacefulness of being high amongst the trees with the glow of the lake and shared sandy beach just steps away.

Guest favorite
Home in Wakefield
4.98 out of 5 average rating, 184 reviews

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Book now and get 10% OFF for weekly or longer stays!

Top guest favorite
The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.
Home in Hollis
4.99 out of 5 average rating, 458 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Top guest favorite
The cabin is nestled among tall trees, featuring a rustic wooden exterior and welcoming warm lighting from the windows. A stone barrier lines the property, while several outdoor chairs offer a comfortable space for relaxation.
Cabin in Denmark
4.95 out of 5 average rating, 207 reviews

Barrett’s Cabin

Welcome to Barrett's Cabin located in the foothills of the White Mountains with water views of Hancock Pond, 50 minutes to Portland, 35 to North Conway and 15 to Bridgton and Pleasant Mountain. Open concept first floor, 2 bedrooms, 1 bathroom, Carriage House has 2 bedrooms. Driveway fits up to 6 cars. Enjoy outdoor patio, shower, fire-pit, private mini hiking trail system and quick access to snowmobile trails and public boat launch 1/3 mi away.

Popular amenities for Wakefield kayak rentals

When is the best time to visit Wakefield?

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Avg. priceG$50,211 GYDG$54,813 GYDG$42,051 GYDG$47,072 GYDG$60,462 GYDG$65,065 GYDG$71,759 GYDG$71,759 GYDG$63,809 GYDG$62,554 GYDG$59,416 GYDG$56,278 GYD
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Quick stats about vacation rentals with a kayak in Wakefield

  • Total vacation rentals

    Explore 40 vacation rentals in Wakefield

  • Nightly prices starting at

    Wakefield vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,560 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Wakefield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wakefield rentals

  • 4.9 Average rating

    Wakefield stays are highly rated by guests—averaging 4.9 out of 5!