Pet-friendly holiday rentals in Sidney

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

Quiet and Private 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—yes, we're pet-friendly! 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.

Roxie the Tiny Cabin on 100 acres

If all you need is a bed and a bathroom, Roxie is the cabin for you! A very comfortable full-size bed, a composting toilet, and a mini woodstove are here for you in this cozy 8x12 cabin in the woods. 2wd vehicle access & a parking spot near your door. Hike trails, kayak, fishing, cross-country skiing, or snowshoeing then return to your little space to relax & enjoy! A firepit with wood, an outside table, hammock chairs, and solar power lights & charging. 24/7 Guest restroom with shower!

Heavenly 4bd farmhouse in Maine.

Medicine Hill is a 125 acre farm on the Sandy river complete with an old fashioned swimming hole and an entire island to explore. We grow a wide variety of vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch taking it all in. 4 bedrooms have incredible views and are surrounded by trees or fields. And if the Chef is available..eat!

Hilltop Retreat with Hot Tub & Sauna near Downtown

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.

Island Glamping in a Luxury Tent in Maine

The Hemlock Haven tent looks out at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, and explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you get settled into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Kate-Ah-Den Cabin, a soul soothing escape.

Secluded & artistically built - a cozy cabin on top of Hampshire Hill. Relax and enjoy the views, take time to hear yourself think, or go explore 75 acres of private woods w 2 miles of private trails. 10 minutes from downtown Belgrade Lakes & public beaches on Long Pond & Great Pond. Close to Kennebec trails, snowmobile trails, Farmington & Augusta. 1 hr south of ski resorts. Great for stopping for 1 night or for taking a week to escape from the world.

Riverside

Overlooking Kennebec River, Riverside is a perfect setting. Open 365 days per year; 2BR, 1 BA, kitchen, DR/common area. Situates 6 comfortably, 8 with use of floor mattresses. Renovated, open concept, our home is wheelchair accessible. We accept Service dogs and will consider family dogs and other pets on a case-by-case; please ask. Owners reside on property in separate building. Outdoor trail cameras in use to monitor exterior of residence only.