Family-friendly holiday rentals in Winthrop

ON HALEY POND - 16 Pond Street, Rangeley, ME

PRIVATE and Upscale apartment in the village walking distance from restaurants, swimming, walking trails, kayak rentals and kayaking as well as snowshoeing and snowmobiling during the winter. Free skate rentals for skating on Haley Pond and you can also rent snowshoes and kayaks at Ecopalagicon. When the pond is frozen SNOWMOBILERS can cross Haley Pond which is in front of my house to get onto trails. My driveway will accommodate 2 snowmobile trailers. 2 night minimum on SNOWDEO WEEKEND

Cottrill House on Damariscotta River #2

A convenient and newly renovated apartment. Enjoy the mid-coast in down town Damariscotta Maine. Private entrance, two bedrooms, private bathroom, living room, kitchen. NO CLEANING FEE! Private back yard with views over the Damariscotta River. Walk to unique restaurants and shops. Rent a kayak or a paddle board across the street and enjoy the beautiful views of the Damariscotta River. Only, 25 minutes away from Pemaquid Point and Beach. 32 miles to Popham Beach and Reid State Park. No smoking!

Cottage style home 2 blocks from the beach!

Comfortable Cottage style home with 3 bedrooms, private baths. Many amenities. Two living areas for everyone's comfort, a beautiful kitchen, a large private outdoor patio with multiple seating, a fire pit and a gas grill. Backyard is partially shared. We are close to the Portland nightlife, airport, shopping, restaurants and family-friendly activities. We are in a community that offers biking , running routes, parks and History. Warm, welcoming home. In law attached with private entrance.

Falmouth 3br near Town landing

Enjoy the rocky coast of Maine with lobster rolls on Town Landing pier. Watch the Lobster fishers work and buy fresh lobster right off the boat. With Portland Maine’s iconic Foodie city with artisan brewers and fun dining and night life just down the road. (6.6 miles) Our classic New England Cape home is the perfect place to meet family and cook and eat around the counter in our amateur chef’s kitchen. Crack some fresh Lobster from Shaws on Rt One they are happy to cook them for you.

Great Modern Space and House

Beautiful house, updated and renovated by the owners. Very nice, quiet and friendly neighborhood on a dead end street. Clean, simple and modern home. Natural light in every space. Nice Bathrooms and updated Ikea kitchen. Open space in living room, very nice fence yard to watch from the living room and for kids to play. Wood and tile floors on the first floor. Carpet only on the bedrooms in the second floor. A lot of Storage and closets to make your stay very comfortable.

Hot tub with country setting, close to village.

Must bring Bathing & hot tub towels We will supply everything else. ALL Major 3 day holiday weekends is a min of 3 nights!! Now close to the new Mt Washington Recreation Path. Country setting, quiet, three bedroom home close to village. All major ski resorts are minutes away. Hiking paths as well as TAX FREE OUTLETS. Brand new hot tub and wood stove works, wood is mostly supplied Storyland and Santa's village is also minutes away. Great country feeling in a good location.

Fall in LOVE With PORTLAND, MAINE

Portland and its surrounding areas is a FOODIE's paradise. Our comfortable home is perfect for Family or Friends to enjoy Portland's charm. Approx 3 miles from Portland Jetport and 90 miles from Boston Logan airport. Walk to downtown or the Old Port on the waterfront. The surrounding areas offer fine beaches and beautiful scenic towns guaranteed to make you want to come back and visit this best kept secret again!

Sweet Retreat: 3 BDR Stylish Home Mins To Colby

This spacious home of approximately 1,200 square feet is just 1.1 miles from I-95 and located on the ground floor of a charming, two family home completely renovated and tastefully furnished in 2020. Here the “modern design” and “charming rustic feel” mix perfectly. BONUS: Guests have access to the backyard! The private yard boasts a patio set, fire pit, garden, fence and trees along the property line.

Sunday River Bethel Village ! Walk to Restaurants

2 Bdrm, 1 Bth, Cozy Rental located in Bethel Village. 400 yds from The Bethel Inn. Walk to Bethel Village Restaurants & Shops. Home is in residential area with plowed sidewalks and well lit street. Ideal for a mature quiet couple or similar who are into skiing / enjoying the Bethel area and respectful of the property and neighbors. small dog ok, no cats.