Family-friendly holiday rentals in Jefferson

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!

Charming, Family-Friendly Historical In Town Home

STR24-11 Sadler House is an in-town historic home located just blocks from Main Street. We have made it truly convenient for families, with flexible sleeping arrangements in three cozy upstairs bedrooms, two full baths, a fully equipped kitchen, large dining table, living room, and sun room. Walk to shops, restaurants, museums and the harbor in minutes. Our house is the perfect home base for exploring all that the beautiful midcoast has to offer. Ask us about free delivery from Ruckus Donuts!

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.

Bay Windows and Willard Beach, 3 BR, 1 BA

Perfect home base for your visit. One block from Willard Beach and next to Scratch Bakery. Beautiful, sunny, 3 BR, sleeps five. Comfortable Tempur-Pedic beds (queen, full, twin), AC, fully stocked kitchen, 42" flat screen TV with Netflix, Wi-Fi. Off-street parking for 2 vehicles and complimentary laundry in the basement. Perfect Willard Beach plug & play vacation only 10-minute drive to Portland, 5 to Fort Williams, and restaurants within walking distance. Family friendly neighborhood.

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.

Maine Waterfront Hideaway

You won't find mobs of tourists here but you will experience a working lobstering village in Maine. Sit back, relax and enjoy the quiet and privacy of 2+ acres at the end of a dirt road with a huge dock located on a tidal cove. Great for family reunions with lots of space and activities for folks of all ages. We focus on making the house comfortable and don't want you to worry about the little things like feet on the couch, water rings on the table or a broken glass. Life happens :-)

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.

Classic Maine, Modern Comfort

NOTE: Summer Bookings are 7 Days from Saturday-Saturday and tend to fill up by February/March or sooner. All the comforts of home while you're away from home. Come enjoy a newly built beach house (2008) just short walk from beautiful Popham Beach - one of Maine's most beautiful and expansive beaches, one hour north of Portland, Maine.