Vacation rentals in Windsor

2 Acre Waterfront w/Canoes & Kayaks, Game Room

Relax at this beautiful retreat situated on 250 feet of private waterfront on Cobbossee Stream(don't let the word "stream" fool you as it's a wide & gorgeous body of water). Home has 2 bedrooms, 1.5 bathrooms, and sleeps 6 guests. Quiet, private property with limited view of any neighbors,. Enjoy the views sitting on the huge deck, or by either of the 2 fire pits. 3 kayaks & 2 canoes here for miles of exploring, including gorgeous Pleasant Pond. Wildlife galore, including bald eagles & loons!

Lake House on Three Mile Pond with Amazing views

Enjoy Three Mile Pond from a private cottage with amazing views, Quiet and private to enjoy Maine the way it should be, deck, dock, kayaks are available, grill, fire pit and wood for the fire. Sleeps 6, 2 Queen size beds in loft and a queen size sleeper sofa on the main floor. Second floor deck with seating Wake up in the morning and walk directly outside to enjoy coffee and breakfast while enjoying the loons. Linens, towels, pillows and blankets supplied, groceries, laundry, restaurants nearby.

Quintessential Maine cabin w/ private waterfront

Experience the historic Fox Glen Cabin with all the 1930s charm—updated with everything you need for a restful lakeside vacation! Enjoy your coffee on the screened-in porch overlooking the water or watch the sunset during a leisurely kayak. 5 minutes from a microbrewery and 15 minutes from the historic downtown & local restaurants. This cozy cabin is pet friendly and perfect for up to 7 people, includes a full kitchen, beautiful stone hearth & gas fireplace, washer/dryer, fire pit, & 2 kayaks.

Maybelle the Tiny Cabin on 100 acres

Maybelle is an 8x18 cabin with a full-size loft bed, a Cubic Mini Woodstove (wood provided), Natures Head Composting Toilet and Jetsetter massaging hot tub. Kayaks, paddle board, & canoe included . Hiking trails (some solar lit) surround your cabin. Outside is a fire pit and a quick path to the water. Maybelle's kitchen has all the cooking essentials and there's a small propane grill outside & the fire pit for cooking. Cell reception is okay in the cabin, wifi is from a Starlink booster!

Perfectly Located 1 Bedroom

Perfectly located in Augusta, walking distance to Hallowell. Step into this beautifully updated one bedroom apartment that blends modern finishes with cozy charm. Don't miss the stylish updates to this 100-year-old house. Features a plush queen bed and a pullout couch for an additional guest. Full bath , stylish kitchen, and a spacious living area including a 55 inch TV with streaming capability. The property is well maintained and managed by inhouse staff. Contact us with any questions.

The Washington Suite on u-pick blueberry farm.

This unique place has a style all its own. No, he didn’t sleep here, Washington that is, but now you can. Our one-hundred-acre farm is located in the small rural village of Washington. It is located just 2/10 of a mile from the village center where the general store, library and town offices are located. Easy commute east to the coast and the must-see towns of Rockland, Rockport and Camden or west to our capitol, Augusta. One hour and forty minutes to Bar Harbor and Acadia national park.

Super cute waterfront cottage

Beautiful four-season waterfront cottage located on the outskirts of Augusta. The main living space has a full kitchen, living room/dining space, bathroom with laundry, and bedroom (queen bed). The walk-out basement, with its own bathroom, offers a cabin-style space to lounge in or as a second bedroom. Or stay outside and enjoy the water views from the second-story deck or ground-level fire pit. Either spot is an amazing place to enjoy the night sky and listen to the loons and eagles!

Modern Cabin on Crie Hill

Unwind at this secluded hillside hideaway. Perched above the valley with sweeping ridge views, this newly built cabin blends comfort with privacy. Begin your day soaking in the outdoor tub as morning mist drifts up from the valley below, or gather around the granite fire pit in the evening while grilling under the open sky. Designed with sustainability in mind, the retreat runs on solar power backed by a quiet propane generator to ensure a worry-free stay even on cloudy days.

Halcyon Ridge

Halcyon Ridge is owned by Lynn & Chuck Hadyniak, who live nearby. Lynn & Chuck moved out of New Jersey years ago to get away from the hustle & bustle, & raise a family in peace. They love Freedom for its quiet & natural beauty, & would love to host people at Halcyon Ridge who also want to escape the noise. Stargazers will be delighted: low humidity, expansive view of the southeastern sky, & next to no light pollution, make for wonderful viewing. Rest. Relax. Recharge.

Lakefront Escape | Private Dock, Kayaks & Fire Pit

Escape to a private waterfront getaway on Three Cornered Pond. Relax on the dock, swim out to the raft, explore by kayak and paddleboard, or unwind by one of two fire pits. This pet-friendly home blends Maine's rustic charm with modern comfort: a gourmet kitchen, arcade games, fast WiFi, and spa-like heated bidets. Ideal for families, friends, couples, or a quiet work retreat. Create precious memories in a warm, welcoming home designed for good times together.

Duck Lane Cottage | Lakefront w/ Dock & Kayaks

Escape to Duck Lane on Threemile Pond—your peaceful, lakefront getaway! Enjoy a private dock, enclosed porch, 2 kayaks, firepit, and a fully stocked kitchen with a Nespresso bar. Cozy up in 2 bedrooms plus a sleeper sofa, with a remodeled bathroom featuring heated floors. Great for fishing, swimming, or relaxing year-round. Just 15 mins from Augusta and close to Maine’s best coastal towns. Book your stay and make lasting memories in a low-tox environment!

Price's Point - Cabin on the water

Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.