Pet-friendly holiday rentals in Oakland

Cozy Cabin on the Carrabassett River

Enjoy four seasons of recreation while staying in a comfortable cabin overlooking the beautiful Carrabassett River. The cabin is nestled in 17 private acres but is close to services and restaurants, trails, and the iconic Wire Bridge. Snowmobile trails are accessible from the cabin, and ATV trails with parking are accessible from nearby Kingfield (6 miles north). Ski Sugarloaf, bike the Carrabassett Valley trails, hike the Bigelow Preserve, or just relax by the river - this area has it all!

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.

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

Driftwood Cottage | Lake Great Pond | Dog Friendly

Welcome to Driftwood Cottage, a haven nestled in a lakeside community on Lake Great Pond, the largest lake in the Belgrade Lakes region. With its prime location just 5 minutes from downtown and 8 minutes from the Belgrade Golf Course, our cozy abode perfectly blends convenience and serenity. Unwind as you take a leisurely 2-minute walk to the dock on Great Pond, complete with private boat launch. Whether you yearn for lakeside serenity or a round of golf, this retreat is your ultimate haven!

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.

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.

Room B with private entrance, bathroom & hot tub

Room B has a full size bed with luxury mattress and private bathroom with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub & sauna in gym. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

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.