
Vacation rentals with a kayak in Winthrop
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Winthrop

Total vacation rentals
Explore 30 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at G$18,818 GYD per night before taxes and fees

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

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Winthrop vacation 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!
Top-rated kayak rentals in Winthrop
Guests agree: these kayak rentals 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)
LocationOutdoor spacesQuiet

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.
LocationOutdoor spacesGrill

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!
Outdoor spacesValueComfort

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
LocationValueHiking

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!
Outdoor spacesValueTV

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.
Outdoor spacesLocationCheck-in

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!
ValueOutdoor spacesAccess

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.
LocationOutdoor spacesBeach

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.
LocationOutdoor spacesSleep quality

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.
LocationOutdoor spacesBathroom

Price's Point - Cabin on the water
Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.
ValueLocationAccuracy

Veedon Fleece on the Lake
Cozy lakefront getaway on Cobbossee Lake, just feet from the water! Sleeps up to 8 across 4 bedrooms, each with a queen bed. Enjoy 2 full baths off the bedrooms plus a convenient half bath downstairs, and a fully stocked kitchen ready for your cooking needs. Parking for 4-6 cars in the driveway. Nestled in a quaint, quiet neighborhood with wonderful year-round neighbors. Pets welcome for $35/night per pet.
Outdoor spacesValueQuiet
Popular amenities for Winthrop kayak rentals
House rentals with a kayak

Moss House: A Modern Waterfront Cabin in the Woods
Outdoor spacesLocationSleep quality

The Loons' Nest: Lakefront oasis w/ hottub
LocationOutdoor spacesCheckout

Maine Waterfront Hideaway
LocationOutdoor spacesFamily

Beautiful Maine Lakeside Cottage
Outdoor spacesLocationTV

Waterfront Farmhouse with Modern Flair!
Outdoor spacesLocationHospitality

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

Lakefront summer getaway for 6
Outdoor spacesLocationHospitality

Sunset Cove I
Outdoor spacesLocationPool
Cottage rentals with a kayak

Lobstermen's ocean-front cottage
Outdoor spacesLocationCondition

Cozy waterfront home on Merrymeeting Bay.
Outdoor spacesLocationRiver

Waterfront Cottage
LocationOutdoor spacesView

Adorable Year Round Cottage - Walk to Town!
LocationOutdoor spacesQuiet

Our charming,oceanfront, Bradford point cottage
LocationValueAir conditioning

Thompson Lake, No Cleaning Fee Pine Point Cottage,
ValueLocationCheckout

Rising Tide Times - quintessential Maine cottage
ValueOutdoor spacesGrill

Coastal Waterfront Cottage in West Bath
Outdoor spacesValueRiver
Cabin rentals with a kayak

McKeen's Riverside Retreat
LocationValueLong stay

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

Lakefront Home w/ Dock | Porter Lake | Sugarloaf
Outdoor spacesLocationView

The Nest at Camp Skoglund
LocationOutdoor spacesSolo travel

Waterfront,Hot tub,Private dock,Freshly renovated
ValueLocationLayout

Webber Pond Cabin LLC
Outdoor spacesLocationAmenities

Peaceful & private waterfront cabin
Outdoor spacesValueWalkability

Maybelle the Tiny Cabin on 100 acres
LocationOutdoor spacesGetting around
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$62,519 GYD | G$71,928 GYD | G$66,910 GYD | G$66,910 GYD | G$63,773 GYD | G$74,646 GYD | G$73,183 GYD | G$72,137 GYD | G$63,983 GYD | G$60,428 GYD | G$60,846 GYD | G$66,910 GYD |
| 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 |
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