
Holiday rentals with a kayak in Winthrop
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Winthrop
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Off-Grid A-Frame - Peaceful w/ Wood Fired Hot Tub
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Maine lakehouse 2.5 hrs from BOS, 40 min Portland
Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. 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, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak
Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $150.

Hammock Haven Island Dome
The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap on a dock in the water, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, and explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you settle into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

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.

The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

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.

Modern Tree Dwelling w/Water Views+Cedar Hot Tub
Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Cozy, Efficiency Apartment with Hot Tub
Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Room B with private entrance, bathroom & hot tub
Room B has a full size bed with luxury mattress and private bathroom with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.
Popular amenities for Winthrop kayak rentals
Holiday House Rentals with a Kayak

Rising Tide Times - quintessential Maine cottage

Lakefront Getaway

Waterfront Gem walkable to Restaurants!

Bright, Vintage Maine Home, Awaiting Adventure!

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Kayak to the Causeway-50s cottage with modern vibe

Waterfront Farmhouse with Modern Flair!

Lakefront: Private Hot Tub, Sauna & Free Massages!
Cottages with a kayak

Gorgeous Romantic Lakefront Getaway

Gorgeous lakefront, sunsets, kayaks, fire pit

Cozy camp near highland lake

Hidden Haven A Rustic Retreat In St. George, Maine

Waterfront Cottage

Cozy waterfront home on Merrymeeting Bay.

Our charming,oceanfront, Bradford point cottage

Peaceful Lakeside Maine Retreat
Cabin rentals with a kayak

Loon Lodge Canaan,ME

Rustic Family Cabin on China Lake

Hobb’s House - Year Round Log Cabin on the Water

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Get away at Crystal Lake

Private cabin w hot tub,skiing,firepit & mountains

Mill Pond Waterfront Cabin On The Way To Sugarloaf

Barrett’s Cabin
Quick stats about holiday rentals with a kayak in Winthrop
 - Total holiday rentals- Explore 30 holiday rentals in Winthrop 
 - Nightly prices starting at- Winthrop holiday rentals start at $91 AUD per night before taxes and fees 
 - Verified guest reviews- Over 1,130 verified reviews to help you choose 
 - Family-friendly holiday rentals- 20 properties offer extra space and kid-friendly amenities 
 - Pet-friendly accommodation- Find 10 rentals that welcome pets 
 - Rentals with dedicated workspaces- 10 properties have a dedicated workspace 
 - Wi-Fi availability- 30 of Winthrop holiday rentals include Wi-Fi access 
 - Popular amenities for guests- Guests love Kitchen, Wi-Fi and Pool across Winthrop rentals 
 - 4.9 Average rating- Winthrop stays are highly rated by guests—averaging 4.9 out of 5! 
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- Rentals with a kayak Kennebec County
- Rentals with a kayak Maine
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- Sebago Lake
- Sunday River Resort
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Belgrade Lakes Golf Club
- Willard Beach
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Cliff House Beach
- Sunday River Golf Club
- Fox Ridge Golf Club
- Black Mountain of Maine
- Hunnewell Beach
- Maine Maritime Museum
- Eaton Mountain Ski Resort
- Brunswick Golf Club
- Bradbury Mountain State Park
- Pebbly Beach
- The Camden Snow Bowl
- Portland Museum of Art
- Farnsworth Art Museum
