Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
The price is CA $118
CA $443 total
includes taxes & fees
May 12 - May 13
Private Dock on Messalonskee Lake: Cozy Cottage!

Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
The price is CA $167
CA $551 total
includes taxes & fees
May 26 - May 27
Rustic Retreat Across From Lake; Family Friendly!

Trout Ponds & Sauna: Unique Log Cabin in Freedom

Trout Ponds & Sauna: Unique Log Cabin in Freedom
3.0 star property
Freedom
The price is CA $249
CA $458 total
includes taxes & fees
May 19 - May 20
Trout Ponds & Sauna: Unique Log Cabin in Freedom
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Find out more about Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we offer vacation rentals close to popular sights in Windsor, or you can go with a more secluded option if you're looking for a relaxing stay. Windsor is known for its shopping and restaurants.

What are some of the best vacation home rentals in Windsor?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: This vacation home rental outside of Windsor is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Kennebec Ice Arena, or get outside and enjoy nature at Kennebec River Rail Trail. In the larger area, you’ll find Kennebec Arsenal and Maine State House.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Windsor. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.