Holiday rentals with outdoor seating in Winthrop

Merrymeeting Midcoast Cabin

RUSTIC-no running water! cabin perfect for exploring all mid-coast Maine has to offer: 3 hours from Boston or Acadia, 1 hour to Portland and Maine’s gorgeous beaches. 10-30 minute drive to Hiking, swim spots, farm-stands, nationally recognized dairy farms, breweries, restaurants. 5 minute walk from a pickleball court. Stargaze in the hammock by campfire, Grill dinner, check out local tide charts to float in canoe or kayak on the Eastern river. Wood fired oven can be rented for additional fee.

Family Getaway in Oxford Hills-Dog Friendly!

Experience this 2BR/2BA retreat, perfect for couples and small families. Nestled among nature, this hillside getaway offers privacy, modern comforts, and a peaceful ambiance. Unwind by the fireplace, fire pit, relax on the deck, or explore the great outdoors with your furry friend (guests may bring 1 dog). Whether you're seeking outdoor adventure or relaxation, this hideaway is the perfect home base for your next getaway. Families of 5 or 6 can be accommodated with the queen size pull out sofa.

Sunset Chalet Lakefront Hot Tub Game Room

Tucked along the quiet shores of Belgrade Stream and Messalonskee Lake, Sunset Chalet is a cozy waterfront hideaway designed for connection, comfort, and joy. Whether you’re sipping morning coffee on the deck, unwinding in your private hot tub, or making memories in the game room downstairs, this is a place to slow down, breathe deeply, and just be. Built for couples, small families, or anyone seeking a four-season retreat, Sunset Chalet is where nature meets nostalgia—and every stay becomes a

Maine lakehouse 2.5 hrs from BOS, 40 min Portland

Beautiful lake living: 2.5 hours from Boston, 40 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $150.

Hilltop Retreat with A/C, Hot Tub & Sauna

Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub or infrared sauna, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

The Rocky Road Camp on East Pond

Welcome to camp life on East Pond. A 1 bedroom home located in Oakland Maine. Your quiet weekend getaway awaits you. Located in central Maine. You will be about a 60 mile drive to the coast or about a 70 foot walk to the lake. Oakland is just a 20 minute drive to Waterville where both Colby and Thomas Colleges are located. East Pond is the host of several area summer camps. The camp will give you beautiful views of the lake. Sit on the deck and enjoy the loons and other lake activity.

Lakeside Cottage in the Heart of Maine

Sitting 125 feet from the east shore of Echo Lake is the Nest at Camp Skoglund. A cozy cottage for two with all of the amenities you will need. Your deck provides a wooded view of the lake and we offer a fully equipped waterfront for your relaxation and fun on the water. If you require lodging for more than two, please inquire. We are open seasonally, starting in early June until Columbus Day or later depending on the weather.

Naughty Dog Private Island Log Cabin

Be all alone on this remote island with 1400 acres of Annabessacook Lake as your backyard. Enjoy pristine surroundings, a rustic, off-the-grid log cabin, with solar lighting and a hot shower. Swimming, boating, fishing, birding, and relaxing by the fire - do it all (or not). Prepare for adventure! Pack light: Bring your vacay clothes, pups, favorite food, & be ready for a blissful, private island get away. It's AWAY away.