
Holiday rentals with a kayak in Winthrop
Find and book unique kayak rentals on Airbnb
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 €77 per night before taxes and fees

Verified guest reviews
Over 1,310 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Winthrop holiday rentals include wifi 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!
Top-rated rentals with kayak in Winthrop
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Off-Grid Cabin with 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- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Cozy Lakefront 3 Bedroom 2 bath home on Sand Pond
Imagine waking up to stunning waterfront views of pristine Sand Pond, perfect for boating and fishing. Located just five minutes from a golf club and grocery store. This 3-bedroom, 2-bathroom cottage is ideal for friends and families looking to come together and enjoy the beauty of Maine. When the sun goes down, toast up some marshmallows on the outdoor propane fire pit. If the weather doesn’t want to cooperate then you can enjoy the full kitchen, covered porch, pool table, and stocked bookcase.

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!

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.

Beautiful lake house on Tacoma Lakes near Coast
Pets NOT allowed to due host severe allergies. Please find a different home if you have a service animal or be charged separate cleaning fee of $800 Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened-in Porch 3 spring fed lakes Private dock Bring boat or local rental Canoe/Kayaks FirePit,Grille, Lawn chairs Provided: linens/towels/soap/shampoo/detergent Smoke-deck only - NO SHOES inside *Must sign separate water front liability waiver after booking No cameras inside or out

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.

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!

Mirror Pond Cottage
A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.

Lakeside retreat on quiet cove on Cobbessee Lake!
Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.

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!).

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 does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Visit Beautiful Home on Snow Pond
Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.
Popular amenities for kayak rentals in Winthrop
House rentals with a kayak

Beautiful Maine Lakeside Cottage

Lakefront summer getaway for 6

The Loons' Nest: Lakefront oasis w/ hottub

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

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

Maine Waterfront Hideaway

Sunset Cove I

Beautiful lakehouse, 2.5 hours from Boston, 40 minutes from Portland
Cottage rentals with a kayak

Lake Great Pond| Dog Friendly | Boat Launch

Coastal Waterfront Cottage in West Bath

Waterfront Cottage

Cozy waterfront home on Merrymeeting Bay.

Rising Tide Times - quintessential Maine cottage

Our charming,oceanfront, Bradford point cottage

The Loon's Nest Cottage

Adorable Year Round Cottage - Walk to Town!
Cabin rentals with a kayak

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Peaceful & private waterfront cabin

The Nest at Camp Skoglund

Lakefront Home w/ Dock | Porter Lake | Sugarloaf!

Waterfront,Hot tub,Private dock,Freshly renovated

Webber Pond Cabin LLC

McKeen's Riverside Retreat

Sunset Chalet Lakefront Hot Tub Game Room
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €257 | €295 | €275 | €275 | €262 | €306 | €300 | €296 | €263 | €248 | €250 | €275 |
| 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 |
Destinations to explore
- Montreal Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Salem Holiday rentals
- Bar Harbor Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- New Haven Holiday rentals
- Sebago Lake
- Popham Beach, Phippsburg
- Willard Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Sunday River Resort
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Portland Museum of Art
- Maine Maritime Museum
- Rockland Breakwater Light
- Bradbury Mountain State Park
- Reid State Park
- Bug Light Park
- Grafton Notch State Park
- Camden Hills State Park
- Farnsworth Art Museum
- Mt. Abram
- Cellardoor Winery
- Maine Lighthouse Museum





