Holiday rentals in Winthrop

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winthrop

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Manchester

4.89 out of 5 average rating, 27 reviews

Lakefront cozy cottages w/ dock, canoe & fire-pit!

Situated a few steps from the water of Lake Cobbossee (Cobbosseecontee), with direct views of the sunset. So close to the lake it feels like you are on a boat. The cottage and bunkhouse are welcoming and very cozy. If you prefer a high-end lake house with lots of modern conveniences, this might not be for you, but it may be exactly what you need to relax and forget all your worries for a while. Curl up inside, hang out by the fire pit, swim off the dock or take the canoe out to spot some loons.

Top guest favourite

Cabin in Chesterville

5 out of 5 average rating, 134 reviews

Off-Grid w/ Wood Fired Hot Tub - 4 Kayaks Included

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)

Guest favourite

Home in Winthrop

5 out of 5 average rating, 13 reviews

Waterfront | Dock | Fire-pit | Laundry!

Spacious four-season lakefront camp on peaceful Dexter Pond in central ME. Enjoy great fishing, canoeing, stand-up paddle boarding, kayaking, or relax and watch the sunsets and loons from the large porch overlooking the pond. The home is in a great location close to Winthrop Center and Wayne (10 mins to local grocery store/ farmers market) 30 mins to Augusta/airport. Many hiking trails nearby and lots of other areas to explore. It's beautiful in all seasons. Private dock, firepit, and laundry!

Top guest favourite

Guest suite in Monmouth

4.97 out of 5 average rating, 158 reviews

Welcome to The Nest - 1 bed, deck w/bath & parking

Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bar & pizzeria. Willows Awake and The Vista wedding venues w/tasting rooms. Microbrewery’s Grateful Grains & Van der Brew tap rooms w/food trucks & entertainment. Maine turnpike access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates,Bowdoin, Colby, Thomas & Husson. Golfing, boating, antiques, State Parks, hiking/walking trails,beaches & Festivals.

Guest favourite

Flat in Winthrop

4.96 out of 5 average rating, 47 reviews

Jill's Place, no cleaning fee!

This is a brand new daylight basement airbnb with access to Cobeeseecontee Lake in Winthrop Me. 2 bdrm. 1 with a queen and 2nd with 2 twins. It is decorated with with white shiplap, beautiful hardwood floors and very light and bright. It is 160 ft from the lakeside where there is a very nice grassy area with lounge chairs, a dock, and a swimming area. 1 kayak and a peddle lboat included. 500 ft away from the Travis Mills restaurant "The White duck" 2 miles from the famous Cabin Masters!

Top guest favourite

Cabin in Readfield

4.98 out of 5 average rating, 54 reviews

Pet-Friendly Lakefront A-Frame

Escape to this charming 3-bedroom, 1-bath A-frame cabin in Readfield, Maine, perfectly nestled in the woods just steps from the pristine waters of Maranacook Lake. Enjoy peaceful days swimming, kayaking, canoeing, and fishing, all while surrounded by nature. The cabin combines rustic charm with modern amenities, featuring exposed wood interiors, new appliances, and Smart TVs. Unwind on the screened-in porch, listen to the loons, and explore nearby trails and the beauty of the Lakes Region.

Top guest favourite

Home in Hallowell

4.98 out of 5 average rating, 130 reviews

Hilltop Retreat with Hot Tub & Sauna near Downtown

Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Top guest favourite

Island in Monmouth

4.99 out of 5 average rating, 227 reviews

Island Glamping in a Luxury Tent in Maine

The Hemlock Haven tent looks out at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap, 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 get settled into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

Top guest favourite

Loft in West Gardiner

4.98 out of 5 average rating, 181 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.

Superhost

Cabin in Monmouth

4.86 out of 5 average rating, 36 reviews

The Woodland Lodge

Looking for a cozy family-friendly get away in the beautiful woods with access to a shared beach on Annabessacook Lake, look no further than The Woodland Lodge. Located in Monmouth ME, the cabin is close to the public boat launch for Cobbosseecontee Lake and Whittier Woods trails. It is 30 minutes to Augusta Regional airport, 1 hour to Portland Jetport, and 90 minutes to Sugarloaf. Enjoy the peaceful woods, shared beach access, and beautiful hiking trails nearby!

Top guest favourite

Cabin in Winthrop

4.97 out of 5 average rating, 69 reviews

Quaint & cozy cabin in beautiful wooded setting

Kick back and relax in this calm, stylish space. Less than 15 minutes to Augusta, and an hour from Portland! Close to many amenities, but far enough out to enjoy nature. The cabin sits on 33 acres, with fields and trails. The cabin itself has Wi-Fi, cable tv, a lofted queen bedroom, all of which have been recently updated. Outdoor amenities include BBQ grill, and lakes and ponds in close proximity.

Guest favourite

Cabin in Winthrop

4.97 out of 5 average rating, 39 reviews

Lake Cabin in the Trees

Quiet lakefront cabin tucked in the woods with shimmering views of Wilson Pond below, the last house on a private dirt road. Dive in for a swim from the private dock or kayak to the lake's small islands. Stay connected with a dedicated office with desk and fast internet. A calm, secluded getaway for any season.