
Vacation rentals with a kayak in Wakefield
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Top-rated kayak rentals in Wakefield
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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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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
House rentals with a kayak

Waterfront Gem walkable to Restaurants!

4-Season Escape w/ Woodstove, Firepit & Mtn Views

Kayak to the Causeway-50s cottage with modern vibe

Cozy camp for swimming, water sports and more!

Waterfront Getaway Home in Epsom, NH

Peaceful 4 bedroom lakehouse retreat

Hot Tub Haven: Dog-Friendly Retreat

Private Waterfront! Views, Hot Tub, King Bed
Cottage rentals with a kayak

Smokey Pines Camp

“Stay Awhile in the Lake's Region”

Cottage on the lake! Includes kayaks & rowboat!

Lovely cottage on Sunrise Lake, Middleton, NH.

Cottage w/ charm, mountain view & river HSI Wi-Fi

Close to skiing, hot tub, beach access & fire pit

RK North : All season Waterfront cottage with dock

Peaceful Lakeside Maine Retreat
Cabin rentals with a kayak

+ Cannon Mountain Collective | Forest Undertones +

Rustic Log Cabin on Pawtuckaway Lake

Little House on the Lake in the Forest

Beautiful private cabin on Big Squam Lake

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Lakeside Cabin Nestled in the Pines

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

Get away at Crystal Lake
When is the best time to visit Wakefield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$50,211 GYD | G$54,813 GYD | G$42,051 GYD | G$47,072 GYD | G$60,462 GYD | G$65,065 GYD | G$71,759 GYD | G$71,759 GYD | G$63,809 GYD | G$62,554 GYD | G$59,416 GYD | G$56,278 GYD |
| Avg. temp | -5°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -1°C |
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!
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- Rentals with a kayak Carroll County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Hampton Beach
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Squam Lake
- Story Land
- Scarborough Beach
- York Harbor Beach
- Weirs Beach
- Attitash Mountain Resort
- Long Sands Beach
- Loon Mountain Resort
- Jenness State Beach
- Rye North Beach
- North Hampton Beach
- Pats Peak Ski Area
- Diana's Baths
- East End Beach
- Dunegrass Golf Club
- Funtown Splashtown USA
- Tenney Mountain Resort
- Willard Beach
- Parsons Beach
- King Pine Ski Area