Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Top guest favorite
A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.
Home in Augusta
4.96 out of 5 average rating, 177 reviews

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!

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 404 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top guest favorite
An open living space features a cozy seating area with a light-colored sofa and a decorative area rug. A spacious bed is placed in one corner, accompanied by soft bedding. The kitchenette is visible in the background, along with a doorway leading to a bathroom.
Apartment in Gardiner
4.98 out of 5 average rating, 160 reviews

The Escape on Elm

Our charming Airbnb is located in the heart of Gardiner Maine. Built in 1850, our historic home combines old-world charm with modern comforts. Enjoy the creaking hardwood floors, exposed beams, and coastal accents that create a calming, seaside vibe. The open layout offers a spacious living room with a sofa bed, Smart TV, books and board games. We offer a comfortable sleeping area with a queen bed. A full bathroom. Enjoy cooking in the fully equipped kitchen that opens to a private porch.

Top guest favorite
A charming two-story building features warm wood siding and a green metal roof. The entrance is framed by a covered porch and surrounded by well-maintained landscaping. Tall trees provide shade in the foreground, enhancing the welcoming appearance of the property.
Apartment in Washington
4.97 out of 5 average rating, 128 reviews

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.

Top guest favorite
A charming red house is visible from the winding driveway, framed by tall trees and patchy grass. The front porch runs along the house, while two garage doors and a wooden structure are located nearby. A dog can be seen walking along the pathway.
Apartment in Nobleboro
4.92 out of 5 average rating, 205 reviews

Finding Joy

This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.

Top guest favorite
The open-concept living area features a comfortable couch and a recliner, complemented by a dining table and modern kitchen appliances. Natural light enters through the windows, illuminating the space that is adorned with neutral tones and wood flooring.
Cottage in Augusta
5 out of 5 average rating, 108 reviews

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.

Top guest favorite
A studio apartment is illuminated by pendant lights, featuring a queen bed with white linens and a decorative pillow. Wooden walls and floors create a rustic ambiance. A kitchenette is visible along one wall, equipped with basic appliances. The entrance to the apartment is to the left.
Cabin in Whitefield
4.95 out of 5 average rating, 102 reviews

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!

Top guest favorite
A modern cabin exterior showcases a deep blue facade and a welcoming entry, highlighted by a wooden deck adorned with an outdoor seating area. The surrounding landscape features various plants and autumn decor, enhancing the serene setting within the woods.
Tiny home in Appleton
4.95 out of 5 average rating, 111 reviews

Little Apple Cabin on 5 acres, amazing stargazing!

Cabins don't come much cuter than Little Apple Cabin. It's as if someone stayed here and *then* invented the word 'CabinCore'. Nestled in the magical woods of Midcoast, Maine, this cabin is the perfect getaway. Located just 25 minutes from the coast, it's the perfect spot for exploring all that the midcoast has to offer. 20 minutes to Camden and Rockland, 25 minutes to Belfast. (No hunting allowed). Surround yourself by the forest, stargaze all night, and rejuvenate in nature.

Guest favorite
The kitchen features wooden cabinets and a granite countertop. A round dining table with four chairs is situated centrally. Stainless steel appliances, including a refrigerator and a stove, are visible, along with various kitchen utensils and supplies arranged on the countertop.
Apartment in Augusta
4.82 out of 5 average rating, 131 reviews

Downtown Augusta - 2 Bedroom - Newly renovated!

Located at the heart of downtown Augusta, this 2 bedroom apartment is a wonderful choice when visiting Augusta Maine with another couple or if you just want more room then your average hotel! This 2nd floor apartment comes fully furnished with brand new furniture, supplies and bedding! The apartment has keyless entry via a keypad with each guests receiving a unique pin. There is free parking and laundry available on site. Enjoy a stylish experience at this centrally-located place.

Top guest favorite
The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.
Cottage in Edgecomb
4.98 out of 5 average rating, 323 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Top guest favorite
A spacious bedroom features a large bed with blue bedding against a dark blue accent wall. Two bedside lamps provide soft lighting. A comfortable leather armchair is positioned next to a small nightstand, which holds a tissue box and a framed print.
Home in Hallowell
4.98 out of 5 average rating, 171 reviews

Hallowell Hilltop Home and Hot Tub

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.

Top guest favorite
The exterior of a charming yellow house is presented, featuring white stairs leading to a green front door with an ornamental design. Lush shrubs frame the entrance, and tall trees provide shade to the vicinity, creating a welcoming appearance.
Home in Waldoboro
4.99 out of 5 average rating, 102 reviews

1830s Cape hosted by George & Paul

This 1830 cape is for rent by the month or weekly or for a two-night minimum stay. It is located at the edge of the historic village of Waldoboro. It offers a convenient base to sightseeing in midcoast Maine. It’s old-fashioned, decorated with plants, antiques and paintings and features a large, fully equipped kitchen, music room with piano, television room with pull-out sofa, full bath with stall shower and outside patio. Your hosts are right across the driveway.

Popular amenities for Windsor vacation rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Windsor