Vacation rentals with a kayak in Messalonskee Lake

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Top-rated kayak rentals in Messalonskee Lake

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Top guest favorite

A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.

Home in Augusta

4.95 out of 5 average rating, 145 reviews

Lakefront: Private Hot Tub, Sauna & Free Massages!

Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

Guest favorite

Chalet in Belgrade

4.98 out of 5 average rating, 107 reviews

Sunset Chalet | Lakefront • Hot Tub • Game Room

Tucked along the quiet shores of Belgrade Stream and Messalonskee Lake, Sunset Chalet is a cozy waterfront hideaway designed for connection, comfort, and joy. Whether you’re sipping morning coffee on the deck, unwinding in your private hot tub, or making memories in the game room downstairs, this is a place to slow down, breathe deeply, and just be. Built for couples, small families, or anyone seeking a four-season retreat, Sunset Chalet is where nature meets nostalgia—and every stay becomes a

Guest favorite

Two kayaks, one yellow and one orange, rest along a grassy shore next to a calm waterfront. Lush green grasses frame the scene, contrasting with the tranquil blue water and distant shoreline, inviting exploration and connection with nature.

Cottage in Topsham

4.93 out of 5 average rating, 248 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Superhost

A spacious yard is seen, featuring two green adirondack chairs positioned near a lakeside fire pit. A small boat is resting on the shore, with clear water stretching out into the distance. Tall trees provide shade and the sky is partially cloudy.

Home in Plymouth

4.82 out of 5 average rating, 61 reviews

Lakefront Maine Camp (year round)

Settle into the quiet ease of Maine in this waterfront house on a private lake with beautiful views from inside and out. Brand new kitchen. Comfortable living spaces and an expansive yard featuring 2 large lawns for family fun, a lakeside fire pit, and small boat launch. Enjoy swimming and fishing along 100' of waterfront or go for a paddle with the canoe, kayaks, and paddle board. Back country hiking along adjacent snowmobile/x-country skiing/ATV trails. This is the getaway you are picturing.

Top guest favorite

Home in Bath

5 out of 5 average rating, 101 reviews

Waterfront Farmhouse with Modern Flair!

On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

Superhost

The exterior of the house features a carport, a spacious gravel driveway, and a screened-in porch. A tranquil view of the lake is seen through trees, with lush green grass leading to the water's edge. The overall setting is peaceful and natural.

Home in Litchfield

4.92 out of 5 average rating, 135 reviews

Beautiful lake house on Tacoma Lakes near Coast

Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

Top guest favorite

Home in Newcastle

4.99 out of 5 average rating, 155 reviews

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Top guest favorite

A rustic dining area features a small table with three wooden stools, positioned near a large window. The window offers a view of the water and outdoor space, framed by wooden shutters that complement the warm wooden walls.

Guesthouse in Newport

4.96 out of 5 average rating, 81 reviews

Cozy Bungalow

Only 25 minutes to Bangor medical facilities We added a cozy addition to our garage for guests to share our water front property. Your own private dock and small beach area Plenty of parking for your Utv or snowmobiles The Rail Trail is at the end of our driveway WiFi BBQ grill Washer and dryer Full-size fridge with freezer Picnic table Kayaks There is no stove to cook on inside, I am trying to avoid food smells inside. There is a new gas grill with side burner for outside cooking

Guest favorite

The yacht, Nebi, is depicted docked on calm waters. Its sleek white exterior is complemented by blue canopy awnings. Surrounding scenery includes charming buildings, suggesting a lively marina environment, while a church steeple is visible in the background against a partially cloudy sky.

Boat in Damariscotta

4.9 out of 5 average rating, 125 reviews

Nebi—Private Yacht on Scenic Damariscotta River

With warm wood interior, Nebi has the comfort of a home and a 360-degree view of the tidal Damariscotta River. Experience a unique Maine adventure, swim right off the boat, or paddle the inclusive kayaks downriver to view everything from seals to ospreys and oyster farms. The quaint twin villages of Damariscotta - Newcastle are a 2-minute stroll away from the private marina with charming restaurants, galleries and a short drive to gorgeous lighthouses, walking trails and beaches.

Guest favorite

A grassy area near the water features several colorful kayaks stacked neatly under a large tree. The sandy beach and the lake are visible in the background, with a clear blue sky overhead. Two red Adirondack chairs are positioned nearby for seating.

Cabin in Burnham

4.93 out of 5 average rating, 80 reviews

The Getaway- A Cozy Lakeside Cabin

Welcome to The Getaway, a charming lakeside rental on Lake Winnecook. Enjoy stunning waterfront views and sunsets from your cozy beachside cabin. With a heat pump to maintain comfortable indoor temperatures, high-speed business-class internet, and Roku TV, you'll have all the comforts of home. Your stay includes a private gas grill, fire pit, and kayaks. Join us at The Lodge and Cabins at Lake Winnecook for the perfect beach vacation in one of our lovely Maine cabins!

Superhost

The exterior of the home is shown from the water, surrounded by trees displaying vibrant autumn foliage. The house features multiple windows and a large deck that leads to stairs sloping down to the water's edge. The reflection of the house and trees can be seen on the calm water surface.

Home in Pittsfield

4.83 out of 5 average rating, 121 reviews

Cozy Waterfront Home With Breathtaking Views!!!

That's right, you're booking for an entire Waterfront home! Our home features a single floor with opened concept and one of a kind waterfront view. Rain or shine, the home offers a spectacular 180 view of nature that is breathtaking! Located in downtown Pittsfield, you are surrounded by all the amenities that you will need! Boating, fishing, hiking, golfing, parks, restaurants, skydiving, brewery, museum, library, farmer market, supermarket and many more to explore!

Top guest favorite

A secluded cabin is nestled among vibrant green trees on a tranquil island. A wooden walkway leads from the dock to the front of the cabin, which features a green metal roof. Two canoes are visible on the calm water, enhancing the serene landscape.

Island in Monmouth

4.98 out of 5 average rating, 229 reviews

Naughty Dog Private Island Log Cabin

Be all alone on this remote island with 1400 acres of Annabessacook Lake as your backyard. It's the Micro Island featured in Jon B. 2022 videos. Enjoy pristine surroundings, a rustic, off-the-grid log cabin, with solar lighting and a hot shower. Swimming, boating, fishing, birding, and relaxing by the fire - do it all (or not). Prepare for adventure! Pack light: Bring your vacay clothes, pups, favorite food, & be ready for a blissful, private island.