Holiday rentals in Dexter

Sugarmaple Lakehouse - Sebasticook Lake Newport ME

Beautiful Mid-coast Maine lakehouse! Relax with friends & family at this peaceful 2.6 acre lakehouse with 260’ of private Sebasticook Lake frontage plus private dock. Built in 1900, Sugarmaple Lakehouse sits back from the water 100 yards on meticulously-cared-for grounds. Grill on the deck, hang out at the fire pit with S'mores. Go kayaking/fishing/ATV through Fall. Enjoy as a winter paradise as well, with skiing just 25 minutes away, snowmobiling & more. Equipped with Smart TV & Amazon Echo.

Cozy Cabin on the Water in Central Maine with WiFi

Cozy traditional cabin on Ripley Pond right in the middle of Maine. If you are looking for a party scene, this is NOT it. Here you can swim, fish (bass!), paddle, relax by the fire pit or in a hammock or curl up with a good book on the deck or in front of the pretty stone gas fireplace. Fully equipped kitchen makes life easy with gas stove, fridge, microwave and dishwasher. There is a washer and dryer in the bathroom. First floor bedroom sleeps 2, and the loft has 2 futons plus a work space.

Cozy Rural A-Frame in the Middle of Maine.

Get away from it all when you stay under the stars. This chalet is right on the ITS trail, nestled in the middle of a small lightly wooded lot in a rural setting. Enjoy the fire pit, bring your snowmobiles, bikes and trailers. The space is cozy with a 55" TV and small kitchen to prepare your meals. The bedroom is in the loft with catwalk opening up to a balcony. Enjoy access to year round outdoor activities as you are nearby Katahdin Iron Works/Jo Mary region and near Sebec and Schoodic lakes

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.

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!

Gorgeous 1897 Maine Barn Near Lake and Hiking

Luxurious 1800s barn in a garden setting with all the modern conveniences. New appliances, Wifi, cable and 75" Samsung smart TV. Soaring vaulted ceiling in extra large master bedroom, kitchen and bathroom. Large living area with two twin beds fit together to make a king. Fabulous grounds. Horseshoes and fire pit are available if no one is renting the Canoe Shop. Next to Y for gym and swimming. Day passes available for $10. Just 10 minutes from beautiful Sebec Lake!

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.

Loft Retreat

Welcome to our enchanting loft retreat! Our thoughtfully designed apartment offers a serene escape with a touch of sophistication. Ascend the spiral staircase to discover a cozy bedroom complete with a work space and reading nook. Hidden up a trap door on the third level are two twin beds for the nimble. A full deck complete with a small fire pit is available in the warmer months. Your getaway awaits!

The Carriage House at Peony Hill

Come stay on the grounds of a 1913 French Colonial in the original carriage house at Peony Hill. The carriage house is a full one bedroom, full bath, kitchen, eat-in dining area, along with spacious living room complete with a cottage/cabin feel. The new June 2022 remodel decor is quaintly appointed with regional Maine finds and vintage antiques scattered in the professional decor.