Family-friendly 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, Fall dates open!

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, a/c, laundry!

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.

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

Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bars & pizzeria. Several wedding venues, Willows Awake & Lupines and Lace. Tasting rms Grateful Grains, Absolem Cider. Food trucks & music. Maine turnpike 95 access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates, Bowdoin, Colby, Thomas & Husson. Golfing & Frisbee, boating, fishing, antiques, State Parks, hiking/walking trails, beaches & Festivals.

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!

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax with ocean views, warm up in the sauna or take a refreshing dip. Our cottage is part of Gurnet Village, an over 100-year-old working lobstering & oyster farming property on historic Route 24, between Brunswick & Harpswell. Expect boats, workers, road traffic, gear, and the occasional sounds & smells of a real Maine working waterfront. All rooms have ocean views, with access to the tidal beach & floating dock (May-Dec).

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

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.

LuxuryTreehouse w/ Hot Tub Near Sunday River

Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.

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.

Private Lake House, Firepit & Amazing Sunset Views

Spring & summer at Lakeshore Point, a private lakefront home on Canton Lake in Maine. Privately set at the end of a quiet lane, this updated modern retreat offers 200’ of pristine waterfront and your own private sandy shoreline. Swim, kayak, and paddleboard by day, then gather around the fire pit at sunset. Thoughtfully designed with a full kitchen, WiFi, and outdoor shower, it’s where family adventure meets relaxed lakeside New England charm.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.