Holiday rentals in Winthrop

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)

Quiet Lakefront Home, Private Dock!

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!

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Jill's Place!

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!

The Cottage at Red Top - Cozy Lakeside Year-Round

The Cottage at 60 Red Top Drive is a cozy, family friendly place to enjoy quality Maine lake-time. You will have direct access to Anabessacook Lake including a sandy beach area. There is also ample yard space for relaxing and playing games. Indoors, the cottage has plenty of room for the family to be comfortable and a full kitchen. The cottage is a private space on its own, or can be rented in combination with The Main House for an extended family getaway! Ice fishing is right outside!

Perfect Maine retreat!

🏡 Experience lakeside tranquility nestled in Hammonds Grove. A short stroll from Cobbossee Lake, this retreat offers the perfect blend of comfort, nature, and convenience. 🛶 Community Amenities • Lake Access: rights to shared waterfront areas, ideal for swimming, fishing, and boating. • Golf Enthusiasts: The Augusta Country Club is just outside your front door, offering convenient access to golfing. • Year-Round Activities: Whether it’s summer water sports or winter snowmobiling.

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.

Cozy Keyes Cottage | Lakefront • Dock • Kayaks

Cozy Keyes Cottage is your peaceful lakefront escape on Cobbosseecontee Lake — a hidden gem in Winthrop, Maine. With a private dock, kayaks, a fire pit, and room for up to five guests, this well-appointed cottage blends comfort and charm with direct access to the water. Whether you’re sipping coffee while listening to the loons, paddling the cove, or gathering around the fire pit under the stars, this is where memories are made — in every season.

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.

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.

Cozy Rock Cabin #thewaylifeshouldbe

*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!

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.