Holiday houses in Dexter

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

The Ultimate Waterfront Cabin Experience in Maine

The sunset views are plentiful here at this cabin. This peaceful retreat is situated on Ripley Pond. It is a wonderful property with much to do, eg, swimming, fishing, reading, floating on the pond, or cooking in our newly outfitted kitchen. The property has a dock and there are four kayaks provided for your use. A boat launch is accessible down the street for you to bring your own water toys. There are many ATV trails for you to bring your four-wheeler. Parties and large gatherings not allowed.

Cottage That Overlooks The Field

Discover The Cottage that Overlooks the Field—a unique Maine retreat blending New England charm, modern comfort, and inspiring natural beauty. Celebrate milestones, reconnect with friends, or find peaceful solitude while experiencing the true essence of Maine—its landscapes, fresh local flavors, and rich cultural traditions. This soulful space invites you to slow down, awaken your creativity, romanticize everyday moments, and leave deeply refreshed, inspired, and connected to life’s simple joys.

Acadia Pines Retreat HotTub-10 Min Downtown Bangor

Hot tub. Nature. Total peace. 🌲Acadia Pines Retreat-just 10 minutes from downtown Bangor and close to Acadia National Park. Warm wood ceilings, curated interiors, and cozy moments in the beautiful Maine woods. This retreat features open-concept living space styled with rich textures, soft lighting, and designer touches throughout. Sink into plush seating, enjoy slow mornings with coffee at the stone island, or unwind after exploring surrounded by stillness of forest in your private hot tub.

Lakehouse 4 season getaway with rail trail access!

You'll love this comfortable retreat on peaceful Lake Wassookeag, and Dexter's small-town charm. Winter, bring snowmobile, XC-ski, or ice-fishing skills; come spring and summer, swim, kayak or paddleboard, from the back yard. The Newport/Dover Rail Trail ("4 season adventure trail") is accessed from the lower yard, great for walking, cycling, snowmobiling, XC Ski, ATV. Come explore "The Heart of Maine", Dexter is only 25 minutes from Route 95, and a gateway to Moosehead, Katahdin, Acadia.

Rustic Country Apartment on The Moosehead Trail.

We recently acquired the house we live in which has an efficiency apartment in the back. It is cozy and private. The house is old and unique. It was previously a long term rental. We wanted to provide a restful space in the heart of Maine Highlands, the crossroads of Central Maine. We enjoy the scenic area with beautiful lakes rivers, multiuse trail systems and trail head of the 100 mile wilderness of the Appalachian Trail, Moosehead lake, Maine's largest lake, and State Parks.

Upta Camp

Take it easy at this unique and tranquil getaway. Take a hike down one of the trails out back, or swim in the cool clear water of the spring fed pond off the back porch. Cozy up during a storm by the fire with a good book, or wet a line on a clear morning off the back steps and catch supper! It’s all in one comfy cabin property to get away from it all. Only a few miles to Dover-Foxcroft, or Sebec Lake. Far enough away to get away, but close enough to the amenities and sights.

The Belle Air

Bring the whole family to this great place with lots of room for fun. Views of Wassookeag Lake. Walking distance to the public beach and boat landing. Close to ITS 85 trails for ATV's. Walking distance to downtown and Main street shops. Enjoy a sunset on the back porch and a sunrise from the enclosed front porch. Local public golf course less than one mile away. Come relax close to parks restaurants and the great outdoors! 20 minutes from Newport and 1 hour from Greenville.

Rail Trail Retreat

Enjoy direct access to the Newport/Dover-Foxcroft Rail Trail from our backyard. Not a rider, enjoy the relaxing cottage feel of our home or venture less than a mile to our “Heart of Maine” small town. Enjoy shops, great eateries and quick lake access for those boaters at the public boat launch. With two bedrooms equipped with queen beds, we also offer extra space in the living room with a daybed & trundle. This home had a complete overhaul in 2022-2023 and is brand new!

Moose Manor

This three story restored 1890 home has been decorated as a love letter to Maine. You’ll find coastal nods, locally inspired artwork, and vintage details that reflect the state’s seafaring heritage and woodland soul. Weathered woods and nautical accents in the interiors for understated cozy elegance. This home offers an authentic Maine backdrop for every season. Great for couples, families, and small groups. Please note that there are NO bedrooms on the first floor.

1890 River Barn

Perched above the Piscataquis River, this historic barn was beautifully renovated into a rustic luxury retreat. Two full stories plus a loft, with relaxing river views on all levels. Gourmet kitchen/dining area with a fireplace & a cozy yet spacious lounge upstairs. Enjoy the garden and patio overlooking the river or unwind in the luxurious copper soaking tub in the loft. Designed for a couple & perfect for romantic getaways, yet comfortable to sleep up to 4 guests.

Relaxing Lakefront Getaway!!!

This 3 bedroom lake house is situated on a SPECTACULAR lakefront lot on Big Lake Wassookeag with a private 132 foot sandy beach with easy water entry. This property was one of the original Dexter Shoe Company camps. Come sit on the deck or down by the beach, enjoy all the waterfront activities, have a campfire while watching incredible sunsets and listening to the loons. You won't want to leave... Just minutes from downtown Dexter.