
Holiday rentals with a kayak in Cumberland
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Top-rated Accommodation with a Kayak in Cumberland
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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.

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym
Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

Maine lakehouse-Ice fishing, skiing, snowmobiling
Beautiful lake living & winter activities, 2.5 hours from Boston, 40 min. from Portland. Near skiing- 1:20 from Sunday River, 1:10 Pleasant Mtn., 1:05 Mount Abram Ski Area, 0:20 Lost Valley. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances. Minutes to Lewiston/Auburn - close to dining and stores. Well known ice fishing spot , cross-country skiing nearby too. Fire pit, great sunsets.

Waterfront Gem walkable to Restaurants!
Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Waterfront Private Apartment only 5 min to LLBean!
Guest apartment with king bed, private entrances, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Cozy log cabin on private pond, near Reid St Park!
Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

Sweet Fern Cabin on Merrymeeting Bay
Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

Beautiful Kettle Cove Apt Steps to Beaches
Enjoy some of the Portland area’s finest destinations year-round. This sunny, 1 BR ground floor apt in Cape Elizabeth has seasonal water views and is nestled between Kettle Cove, Crescent Beach, and Two Lights State Parks. Fields, forests and ponds are a stroll away while downtown Portland is an easy 15-minute drive. The apartment is a great base to explore Southern Maine from and an equally great location to chill out and soak in coastal Maine’s restorative water and air.

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.
Popular amenities for Cumberland kayak rentals
Holiday House Rentals with a Kayak

Mirror Pond Cottage

Rising Tide Times - quintessential Maine cottage

Forest Lake Cottage

Kayak to the Causeway-50s cottage with modern vibe

Waterfront Farmhouse with Modern Flair!

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

Cozy 1BR w/ water access

Spacious Lakehouse +Private Dock+Firepit+Kayaks
Cottages with a kayak

Gorgeous Romantic Lakefront Getaway

Tranquil waterfront cottage

Lovely cottage on Sunrise Lake, Middleton, NH.

Tiny Lakefront Cottage

RK North : All season Waterfront cottage with dock

The Loon's Nest Cottage

Beautiful Lakeside Cottage

RiverPine Retreat - Clean & Bright Waterfront Home
Cabin rentals with a kayak

McKeen's Riverside Retreat

The Conscious Cabin

Get away at Crystal Lake

Private cabin w hot tub,skiing,firepit & mountains

Peaceful & private waterfront cabin

Bear Cabin

Price's Point - Cabin on the water

Roxie the Tiny Cabin on 100 acres
Quick stats about holiday rentals with a kayak in Cumberland

Nightly prices starting at
Cumberland holiday rentals start at $215 AUD per night before taxes and fees

Verified guest reviews
Over 190 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Cumberland rentals

5 Average rating
Cumberland stays are highly rated by guests—averaging 5 out of 5!
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- King Pine Ski Area
- Cranmore Mountain Resort
- East End Beach
- Willard Beach
- Pemaquid Point Lighthouse
- Short Sands Beach
- Diana's Baths
- Gooch's Beach
- Coastal Maine Botanical Gardens
- Funtown Splashtown USA
- Cape Neddick Beach
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Palace Playland
- Conway Scenic Railroad




