
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.

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!

The Nest at Camp Skoglund
Sitting 125 feet from the east shore of Echo Lake is the Nest at Camp Skoglund. A cozy cottage for two with all of the amenities you will need. Your deck provides a wooded view of the lake and we offer a fully equipped waterfront for your relaxation and fun on the water. A fire pit is also available. If you need lodging for more than 2, please inquire about our other cabin, Pop's (also on AirBnb). We are open seasonally starting in early June until Columbus Day or later depending on the weather.

Off-Grid Escape. Wood Fired Hot Tub. 4 Kayaks
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)

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.

Riverside
Overlooking Kennebec River, Riverside is a perfect setting. Open 365 days per year; 2BR, 1 BA, kitchen, DR/common area. Situates 4 comfortably, 6 with the use of couches, 8 with added use of floor mattresses. Renovated, open concept, our home is wheelchair accessible. We accept Service dogs and will consider family dogs and other pets on a case-by-case; please ask. Owners reside on property in separate building. Outdoor trail cameras and AOSU cams in use to monitor exterior of residence only.

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.

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Stella the Studio Apartment
Stella is a cabin-style, pet-friendly studio apartment on 100 acres of wooded property. Enjoy the property's amenities (trails, kayaking, canoeing, axe throwing, wood-fired pizza oven) and return to your comfortable space with a hot tub, power, heat, and plumbing! Stella is located at the start of the land, above our storage building, has plenty of parking and can be reached with 2wd vehicles. This is a new space, exterior is unfinished. The hot tub is an Aqualiving 3 person lounge!

Modern Treehouse 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.

LuxuryTreehouse w/ Hot Tub Near Sunday River
Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.
Popular amenities for Winthrop kayak rentals
Holiday House Rentals with a Kayak

Mirror Pond Cottage

Lakefront summer getaway for 6

Elevated 4-Season home - Mtn Views +A/C + Firepit

The Loons' Nest: Lakefront oasis w/ private dock

Waterfront Farmhouse with Modern Flair!

Beautiful lake house on Tacoma Lakes near Coast

Farm house, River, Island, animals & private Chef.

Sunset & Lake View, Theater, HTub, Xbox, Mini Golf
Cottages with a kayak

Gorgeous Romantic Lakefront Getaway

Lakefront Home, Sandy Beach, Belgrade Lakes

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Coastal Waterfront Cottage in West Bath

Hidden Haven A Rustic Retreat In St. George, Maine

Lake Great Pond| Dog Friendly | Boat Launch

Cozy waterfront home on Merrymeeting Bay.

Our charming,oceanfront, Bradford point cottage
Cabin rentals with a kayak

Lakefront Stunning Home, only 35 min to Sugarloaf!

Sister a-frame in Woods (A)

McKeen's Riverside Retreat

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

Rustic Family Cabin on China Lake

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Get away at Crystal Lake

Peaceful & private waterfront cabin
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $417 AUD | $480 AUD | $446 AUD | $404 AUD | $381 AUD | $459 AUD | $488 AUD | $481 AUD | $427 AUD | $403 AUD | $406 AUD | $446 AUD |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
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 $167 AUD per night before taxes and fees

Verified guest reviews
Over 1,220 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, Wifi 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
- Rentals with a kayak United States
- Sebago Lake
- Sunday River Resort
- Popham Beach, Phippsburg
- Willard Beach
- Popham Beach State Park
- Pemaquid Beach
- East End Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- Pleasant Mountain Ski Area
- The Camden Snow Bowl
- Rockland Breakwater Light
- Portland Museum of Art
- Bradbury Mountain State Park
- Maine Maritime Museum
- Mt. Abram
- Farnsworth Art Museum
- Bug Light Park
- Grafton Notch State Park
- Camden Hills State Park
- Cellardoor Winery
- Pineland Farms
- Maine Mineral & Gem Museum





