Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite

A wooden dock extends into a serene lake, surrounded by a tranquil mist. The surface of the water reflects the soft colors of dawn, while a large floating raft is visible just beyond the dock. The peaceful setting invites relaxation.

Cabin in China

4.89 out of 5 average rating, 177 reviews

Rustic Family Cabin on China Lake

This rustic cabin has been in my family for 4 generations. It's well loved, a bit quirky, sometimes musty and perfect for a family get away. We welcome well trained dogs, and have high expectations that you will respect the place and leave it in good shape for us and future guests. We welcome families, but after bad experiences, we are not available for your reunion or bachelor/(ette) party. Please note we ask you to bring your own sheets and towels. The water in the cabin is not drinkable

Guest favorite

Home in Augusta

4.95 out of 5 average rating, 155 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

Cabin in Dresden

4.98 out of 5 average rating, 243 reviews

Merrymeeting Midcoast Cabin

RUSTIC-no running water! cabin perfect for exploring all mid-coast Maine has to offer: 3 hours from Boston or Acadia, 1 hour to Portland and Maine’s gorgeous beaches. 10-30 minute drive to Hiking, swim spots, farm-stands, nationally recognized dairy farms, breweries, restaurants. 5 minute walk from a pickleball court. Stargaze in the hammock by campfire, Grill dinner, check out local tide charts to float in canoe or kayak on the Eastern river. Wood fired oven can be rented for additional fee.

Guest favorite

A massage room features a treatment table covered with a turquoise blanket, offering a serene atmosphere. Natural light enters through the window, illuminating the wooden shelves filled with massage supplies. A chair and plants add to the calming environment, while a patterned rug complements the wooden floor.

Guesthouse in Appleton

4.9 out of 5 average rating, 298 reviews

Raven's Crossing - Retreat Cottage

Welcome to Ravens' Crossing , an 1850's farm located in Midcoast Maine in Appleton. With two guest cottages to choose from, you will find yourself in a peaceful, quiet space. Hot tub is working! Breakfast is $40, delivered to your cabin. Shared bath at studio, short walk from cabin; out-house at cabin Whether you choose to receive massage, relax in the sauna, stay in a cottage, you can decide how your retreat desires may be met. Retreat cabin is off-grid. There is a studio apartment for guests

Guest favorite

A warm wooden interior features a dining table surrounded by chairs, positioned near large windows that invite natural light. A small side table holds a mirror and vintage wash basin, while rustic decor adds character. The wooden floor enhances the cozy ambiance of the space.

Guesthouse in Washington

4.95 out of 5 average rating, 147 reviews

Fox and Bird Retreat on Davis Stream

Our off-the-grid, solar-powered cottage is nestled within our 18 acres in the town of Washington, Maine. The cottage borders a beautiful stream, is surrounded by tall pines and is several hundred feet away from our home, providing a very private and serene experience. Guests can wander or snowshoe on our property, relax in the screen house next to the cottage or hang by the accessible fire pit. We are close to many local lakes and hiking trails and only 30 minutes from Camden & Rockland.

Top guest favorite

A rustic outdoor fire pit is surrounded by a circle of natural stones, providing a designated area for gatherings. A grate is positioned over the pit, adding functionality for cooking. Soft earth and leaves cover the ground, blending seamlessly with the surrounding greenery.

Cabin in Whitefield

4.98 out of 5 average rating, 120 reviews

Roxie the Tiny Cabin on 100 acres

If all you need is a bed and a bathroom, Roxie is the cabin for you! A very comfortable full-size bed, a composting toilet, and a mini woodstove are here for you in this cozy 8x12 cabin in the woods. 2wd vehicle access & a parking spot near your door. Hike trails, kayak, fishing, cross-country skiing, or snowshoeing then return to your little space to relax & enjoy! A firepit with wood, an outside table, hammock chairs, and solar power lights & charging. 24/7 Guest restroom with shower!

Top guest favorite

A wooden staircase, painted in gray, descends alongside a house. Sunlight casts shadows on the steps. Lush greenery and trees are visible in the background, alongside glimpses of a driveway and outdoor items.

Apartment in Gardiner

4.97 out of 5 average rating, 113 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 row of colorful Adirondack chairs lines a wooden pier overlooking a serene river. The chairs, in shades of green, yellow, and red, contrast with the autumn foliage on the opposite shore. Soft clouds float above, casting reflections on the water's surface.

Home in Hallowell

4.98 out of 5 average rating, 130 reviews

Hilltop Retreat with Hot Tub & Sauna near Downtown

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 or infrared sauna, 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

An exterior view displays a newly constructed set of wooden stairs leading to a deck above. The stairs are framed with pale wooden railings and are flanked by a red building. The sky is bright with scattered clouds.

Apartment in Nobleboro

4.92 out of 5 average rating, 183 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.

Guest favorite

Farm stay in Whitefield

4.83 out of 5 average rating, 335 reviews

Rustic Cabin on Maine Farm

We look forward to welcoming you to our beautiful farm. The cabin has a great connection to nature. It is a quiet, cozy and romantic place. The cabin has a queen bed in the downstairs bedroom and a double bed in the loft. The couch also folds-out to double bed in the sitting room. When reserving the cabin, please register all people over 2 years old. The cabin does not have any heat, but we provide loads of comfy blankets and warm tea to make sure you are comfortable.

Top guest favorite

The living area features cozy seating arrangements including two plush sofas and an armchair. Large glass doors open to a porch, allowing natural light to brighten the space. Knotty pine walls and a warm wooden floor create a welcoming ambience, complemented by a propane fireplace.

Cabin in Augusta

5 out of 5 average rating, 72 reviews

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.

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 314 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

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Popular amenities for Windsor vacation rentals

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Other great vacation rentals in Windsor

Guest favorite

A bright kitchen features white cabinetry and a granite countertop. Stainless steel appliances, including an oven and a kettle, are positioned along the counter. Natural light enters through multiple windows, enhancing the space, while a patterned rug adds texture to the floor.

Home in China

4.93 out of 5 average rating, 14 reviews

Hillside Cabin

RaymondRating, 5 stars1 month ago

The home looked exactly like the pictures, beautiful and stocked with everything you'd need for a good stay. The hosts were super quick and responsive, we had a small minor problem and someone was over right away to fix it super quickly and effectively. Beautiful scenery and 10/10 place to stay when visiting maine ❤️

Guest favorite

A triangular window offers a view of the surrounding woods, with bare trees visible outside and a soft overcast sky. Inside, a cozy corner features a green quilted pillow resting against a bed frame, accentuating the cabin's wooden interior.

Cabin in Oakland

4.96 out of 5 average rating, 71 reviews

Sister A-Frame in Woods (A)

MaryamRating, 5 stars6 days ago

Really cute A-frame, just like the pictures. Everything was spotless and we especially appreciated having tv as it was a rainy day when we arrived. If you’re looking for a glamping experience this is as good as it gets. Peaceful, private, clean with all amenities!

Guest favorite

A charming entrance to the cottage is framed by colorful flower beds, featuring purple coneflowers and daisies. Large glass doors invite natural light, while window boxes filled with blooming flowers add a vibrant touch to the dark exterior of the cottage.

Cabin in Union

4.82 out of 5 average rating, 62 reviews

Drift Cottage near the coast

JocelynRating, 5 stars2 weeks ago

Such a beautiful stay! The shower bag was a surprisingly delightful experience. The place was exactly as described , the view was amazing , and it was only about 25 minutes from Camden which was a beautiful place to go!

Aerial view of a serene lake surrounded by lush greenery, showcasing a blend of trees and natural landscape. The calm water reflects a clear blue sky, while a secluded area of land is visible at the shoreline, highlighting the peaceful environment.

Home in China

5 out of 5 average rating, 3 reviews

Charming Antique Cape

MichelleRating, 5 stars5 months ago

Dianna’s place was lovely offering lots of space - family room, bedrooms, bathrooms, extra rooms to spread out if you need some privacy. Very convenient with a full bath and laundry on the first floor, a bedroom and half bath on the second floor. Outside space for more than one car. Close to Augusta and other surrounding towns. Dianna was very responsive. We had a great few days.

Top guest favorite

Two chickens are spotted in a grassy field during sunset. A rooster stands proudly beside a hen, with a greenhouse and trees in the background, showcasing the natural beauty of the farm's landscape.

Guesthouse in Jefferson

4.97 out of 5 average rating, 64 reviews

Oasis Family Farm Near Hidden Valley

NathanRating, 5 stars2 weeks ago

Absolutely loved staying here. They really have a wonderful setup, and the hosts are incredibly friendly, as are all of the animals on the farm. One of the best Airbnbs I’ve ever stayed in, hands down.

Guest favorite

Home in Georgetown

4.96 out of 5 average rating, 23 reviews

Breathtaking Bay Views!

ColletteRating, 5 stars8 months ago

I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

Guest favorite

A two-story lakefront cottage is depicted, featuring a grey exterior with white accents. The structure is surrounded by tall trees, and a small balcony is accessible from the upper level. A grassy area leads to the front steps, inviting guests to explore.

Home in China

4.83 out of 5 average rating, 6 reviews

Lakefront Cottage on China Lake

JenniferRating, 5 stars2 days ago

We had a great stay at Jessica's cottage by the lake! Very friendly host, responsive, and patient with our questions before booking. The house was spotless, well cared for, and decorated aesthetically. Game room was a bonus! The location was perfect. You can't beat waking up to a serene lakeside view while enjoying your morning cup of coffee. We had everything we needed during our short stay, and check-in/ check-out instructions were clear. We definitely recommend and would book again this summer if we return to the area!

Top guest favorite

A spacious wooden deck extends alongside the building, surrounded by trees. A table with four chairs is positioned at one end, offering a spot for outdoor dining. A brown dog is seen near the edge, with a green tennis ball on the deck.

Apartment in Palermo

5 out of 5 average rating, 16 reviews

Valley View

LauraRating, 5 stars1 month ago

Marks place had everything needed for a long term stay. He and his dog Luna were friendly and didn’t mind the company of another dog. There was an unexpected amount of lady bugs in the home but Mark explained they are a constant battle in Maine and made suggestions on how to reduce/eliminate them as they got in. Highly suggest the meadery up the street. They use locally sourced ingredients and release their weekend menu each Thursday.

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Vacation rentals in Windsor

Top-rated vacation rentals in Windsor

Vacation rentals for every style

Popular amenities for Windsor vacation rentals

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