
Holiday houses in Windsor
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Top-rated holiday rentals in Windsor
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Lakefront: Private Hot Tub, Sauna & Free Massages!
Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

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.

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

The Adams Suite on U-pick Blueberry Farm
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, village church, library, and town offices are located. Beautiful Washington Pond boat landing is only 4/10 of a mile away. Easy commute East (30 minutes) to the coast and must see towns of Rockland, Rockport and Camden or West (30 minutes) to our capitol Augusta. One hour and forty minutes to Bar Harbor and Acadia National Park.

Modern Hideaway in Augusta
Centrally located modern guest home in Augusta, access points to Portland, Midcoast Maine, and Bangor. Spacious master bedroom with closet, additional bedroom, both bedrooms with queen size beds. Handicap bathroom equipped with grab rail and also handicap accessible shower with sit down bench. Many brand new amenities. 55 inch TV has Roku with access to Netflix , Disney Plus, and more! Strong WiFi with the ability to work remotely if needed and explore Augusta and surrounding area.

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!

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Stella the Studio Apartment
Stella is a cabin-style, pet-friendly studio apartment on 100 acres of wooded property. Enjoy the property's amenities (trails, kayaking, canoeing, axe throwing, wood-fired pizza oven) and return to your comfortable space with a hot tub, power, heat, and plumbing! Stella is located at the start of the land, above our storage building, has plenty of parking and can be reached with 2wd vehicles. This is a new space, exterior is unfinished. The hot tub is an Aqualiving 3 person lounge!

One bedroom apartment in rural Waldo County, Maine
A peaceful and scenic setting amidst hay fields in Palermo, ME, a rural location in Waldo County. Central and Mid-coast Maine travel distances (mi.): Waterville: 20; Rockland: 34; Augusta: 24; Belfast:26. The building's lower apartment is dedicated to Airbnb guests. Notes: Smoking is not permitted anywhere on the premises! Evening restaurant options are available only in the locations listed above. There are six entrance steps. Please provide advance notice regarding pet(s)!

Lakefront Retreat in Augusta Cozy Getaway
Welcome to a waterfront getaway on Three Cornered Pond! Relax with panoramic shoreline views, grill dinner on the lakeside patio, and sit by the fire area under the stars. Enjoy arcade games, fast WiFi for streaming or remote work, AC, plush towels, toiletries, and a fully stocked kitchen. Close to Augusta and Portland, surrounded by nature - perfect for couples, families, and remote work. Create precious memories in a warm, welcoming home designed for good times together.

Hallowell Hilltop Home with Hot Tub & Sauna
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, 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.

Little Apple Cabin on 5 acres, amazing stargazing!
Little Apple Cabin is a private tiny cabin on five wooded acres, created for guests who want quiet, space, and deep rest. Surrounded by trees and farmland, it’s a simple, intentional place to slow down, sleep well, and enjoy Maine without crowds or noise. The cabin features a king bed on the main level, a cozy wood stove, and a wrap-around cedar deck for coffee, reading, and stargazing. Camden and Rockland are about 25 minutes away, and Belfast is about 30 minutes.
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Cozy Waterfront Cottage

Camp SugarBear

Lakefront Retreat | Water Views + Private Dock

House in the woods

Perfectly Located 1 Bedroom

Off-Grid Oasis with Ocean Views, Near Rt. 1

Lakefront Cottage on China Lake

Downtown Augusta - 1 Bedroom Loft
Destinations to explore
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- Popham Beach, Phippsburg
- Popham Beach State Park
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Bradbury Mountain State Park
- Rockland Breakwater Light
- Maine Maritime Museum
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Pineland Farms
- Moose Point State Park
- Reid State Park
- Samoset Resort
- Maine Lighthouse Museum
- Range Ponds State Park





