Holiday rentals in Winthrop

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Top-rated holiday rentals in Winthrop

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Top guest favourite

Cabin in Chesterville

5 out of 5 average rating, 141 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)

Top guest favourite

Home in Winthrop

5 out of 5 average rating, 20 reviews

Right on the Lake | 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

4.98 out of 5 average rating, 177 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

Home in Monmouth

4.9 out of 5 average rating, 70 reviews

Spacious Lakeside Comfort - Fall/Winter Wonderland

This spacious home is just steps from the shore of Anabessacook Lake. Here you will enjoy the comfort and luxury of a well-equipped house, surrounded by the best of what Maine has to offer. The Red Top House features an incredible stone fireplace, large screened porch, and stone patio with outdoor fire pit. Bedrooms are comfortable with water views. The kitchen is very well equipped for the whole family. Rental includes use of non-motorized boats and firewood. Ice fishing is steps away!

Guest favourite

Flat in Winthrop

4.96 out of 5 average rating, 57 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

Island in Monmouth

4.98 out of 5 average rating, 242 reviews

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, 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.

Guest favourite

Flat in Augusta

4.81 out of 5 average rating, 124 reviews

Downtown Augusta - 2 Bedroom - Newly renovated!

Located at the heart of downtown Augusta, this 2 bedroom apartment is a wonderful choice when visiting Augusta Maine with another couple or if you just want more room then your average hotel! This 2nd floor apartment comes fully furnished with brand new furniture, supplies and bedding! The apartment has keyless entry via a keypad with each guests receiving a unique pin. There is free parking and laundry available on site. Enjoy a stylish experience at this centrally-located place.

Superhost

Cabin in Monmouth

4.87 out of 5 average rating, 38 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

4.98 out of 5 average rating, 81 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.

Superhost

Home in Winthrop

5 out of 5 average rating, 5 reviews

Serene Lakeside Retreat

Relax with the family at this peaceful lakefront retreat on Cobbosseecontee Lake. Lovingly remodeled with care, this cozy 2-bedroom cottage blends Maine cabin charm with modern updates. Enjoy a full kitchen, spacious living area, two baths, a screened porch, and a deck with stunning lake views. Kayaks included! Unwind, explore, and make lifelong memories at this beautiful waterfront escape.

Guest favourite

Cottage in Winthrop

5 out of 5 average rating, 16 reviews

Little Landing Cottage Lakefront Dock Kayaks

Cozy lakefront retreat with dock, kayaks, and sunsets. Walk to marina & restaurant. Pet-friendly and peaceful year-round. Slow down, breathe deep, and let the lake carry your worries away. This charming cottage invites you to reconnect—with nature, loved ones, and yourself. Perfect for couples, small families, or close friends seeking a cozy and quiet escape just steps from the water.

Guest favourite

Cabin in Winthrop

4.98 out of 5 average rating, 42 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.