Family-friendly holiday rentals in Winslow

‘Round the Bend Farm - private, modern cabin

Our newly built, modern cabin offers a secluded and relaxing retreat in Union, Maine. With the high ceilings, open floor plan, and many windows, guests are surrounded by natural light and forest views. The cabin has a fully equipped kitchen, a cozy fireplace, and an outdoor grill and fire pit. Walking trails connect the cabin to our farm next door, where you can visit with our horses, donkeys, goats, chickens, and ducks. We are just 25 minutes from the Midcoast's shops, restaurants, and beaches.

Off-Grid Escape. 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- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

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.

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Camp at Shale Creek Homestead

Stay with us at Shale Creek homestead! No cleaning fee!! Come enjoy the charm of rural Maine! Countless beautiful ponds and lakes minutes away. Spectacular views of the Milky Way on clear nights and much more! Short drives to the Belfast/costal areas and Augusta. A manageable distance from the mountains of western Maine. Beautiful Branch pond at the end of the street. Lake St. George and China Lake under 10 minutes away. A Great location to enjoy Maine Kayak rentals available on site

Hand built cabin overlooking a pond

Beautiful hand built cabin, overlooking Cotton Pond. Ten minutes from Camden, the sailing mecca of the east coast. Solar lights, (we are off the grid) gravity fed kitchen water, gas-hot water outdoor shower, outhouse overlooking the forest. Hiking trails everywhere! Swimming across the road on Hobbs Pond. If you book in November, there is a possibility that if it gets cold, you will not have a hot outdoor shower and will use water from a 5 gallon ceramic container for drinking and cooking.

Sister a-frame in Woods (A)

Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Check out our other listings managed by Hall’s Homes RE online!

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv/Apple TV. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Brook Ridge Retreat

Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Sweet Retreat: 2 BDR Home Mins to Colby

Minutes from from Colby College (1.5 miles) , Inland Hospital (1 mile), Maine General (2 miles), Exit 127 on I-95 (5 miles). Forced air heat, WiFi, TV (Hulu & Netflix).The apartment is in a quiet, family friendly Waterville neighborhood on the second story of a two family home- has a private entrance, parking, two bedrooms (queen beds), one bathroom (full bath), dining area, fully equipped kitchen ( stove, oven, microwave), Screened in porch and patio.

Sterling House

1960’s Cape in a quiet, centrally located neighborhood. We are licensed with the City of Waterville as a STR. Sleeps (7) comfortably. Less than two miles to Waterville’s Downtown area with several restaurants and bars, Waterville Opera House, Colby College, Thomas College as well as MaineGeneral Thayer Hospital. We are a pet-free home with NO central A/C - fans only. Landscaping: We have a lawn service every other Wednesday between 7:30am and 9am.

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.