Windsor Vacation Home Rentals from CA $209: Search Top Private Vacation Homes for Rent

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Our top choices for Windsor vacation homes

A wooden deck with a railing and steps leading to a house.

1. Home Away From Home. Family friendly, comfortable- centrally located in Augusta

Augusta

CA $377 total

includes taxes & fees

Nov 11 - Nov 12

A wooden cabin with a porch, a rocking chair, and a table with a lantern.

2. Naughty Dog Private Island Log Cabin

Monmouth

"Honestly, this property and the whole experience exceeded all my expectations (which were already pretty high). Kent and the team were so accommodating, making sure that we had everything that we needed and were available at any time. They made special plans to accommodate some friends for a day visit and were so kind and helpful. The property itself was so perfect for what we wanted and the dog so enjoyed the freedom that only a private island can bring! Thanks, Kent, for a very memorable stay....

Peter O.

A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

3. China Lake, Dog Friendly, Lots of space for family gatherings

China

Anne S.

CA $825 total

includes taxes & fees

Nov 15 - Nov 16

A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

4. Cozy House in the heart of Waterville Maine.

Waterville

Rebecca B.

CA $345 total

includes taxes & fees

Nov 15 - Nov 16

A living room with a fireplace, a mounted TV, and bookshelves filled with books.

5. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Nobleboro

Rhiannon A.

CA $542 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with outdoor furniture, a large potted plant, and string lights.

6. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Oakland

Shana S.

CA $340 total

includes taxes & fees

Nov 13 - Nov 14

A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

7. Once Upon a Time — A Peaceful Maine Escape

Freedom

CA $616 total

includes taxes & fees

Nov 17 - Nov 18

A cozy living room with a large window, a leather armchair, a beige sofa, and a wooden coffee table.

8. Readfield Retreat w/ Lake Maranacook Views!

Readfield

Kevin P.

CA $695 total

includes taxes & fees

Nov 10 - Nov 11

A covered deck with large windows overlooking a lake, a boat on the water, and a forested shoreline.

9. Camp Lintonia on Tacoma Lakes

Litchfield

Sandra R.

CA $416 total

includes taxes & fees

Nov 30 - Dec 1

A wooden porch with a door, steps, and potted plants.

10. Renovated Year-Round Lake Retreat on Annabessacook Lake

Monmouth

"We had a wonderful stay! The space was incredibly cozy, comfortable, and welcoming. Ryanne was an absolutely fantastic host. She was attentive, extremely responsive, and so accommodating throughout our stay. Her kindness and generosity really stood out, and she went above and beyond to make sure we had a great experience. The place was also thoughtfully stocked with so many toiletries and essentials, which was especially helpful since I had forgotten a few things of my own! It’s clear that...

Elizabeth D.

CA $460 total

includes taxes & fees

Nov 10 - Nov 11

A large, two-story house with a well-lit front porch and multiple windows.

11. Elizabeth Cottage

Mount Vernon

CA $586 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living area with a wooden ceiling, a dining table with chairs, and a kitchen area with white cabinets.

12. 3 Bedroom Happy Cottage 15

Edgecomb

Dan L.

CA $625 total

includes taxes & fees

Nov 10 - Nov 11

A house with a white front door, a wreath, and flower boxes on the windowsills.

13. Arden Cottage

Mount Vernon

CA $586 total

includes taxes & fees

Nov 10 - Nov 11

A small, single-story house with a white exterior and a dark roof. It features a front door, two windows with shutters, and a small porch area.

14. Nightingale Cottage

Mount Vernon

CA $586 total

includes taxes & fees

Nov 10 - Nov 11

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Top reviews in Windsor

Maine Evergreen Hotel, an Ascend Collection Hotel

Augusta

10/10 Excellent

Tiffany

A wooden cabin surrounded by snow-covered trees and a clear path leading to it.

Clary Lake Bed and Breakfast

Jefferson

10/10 Excellent

Such a special and quiet spot. We were looking for a place to stay for a few nights for an event in Augusta (25 min away) and found this gem. Linda and Rick were welcoming and kind hosts, and breakfast included the best homemade muffins and cider. We met a few fellow travellers and it was a really pleasant and unique experience that we’ll remember. We did wish there were more dining options nearby but the plus side is a very quiet location where you can read on the porch and hope to get a visit...

Kelsey

A modern hotel with a glass facade, outdoor seating area, and a well-lit entrance.

Lockwood Hotel

Waterville

10/10 Excellent

Hotel was clean and modern, with everything you need for an overnight stay. The personal highlight of our overnight stay was the bed - the king room bed was so comfy, I even asked for the mattress details upon check out! The Lavazza coffee/coffee maker made the best cup of in room coffee I have had. Hotel staff were friendly and accommodating (from the front desk to the restaurant). Free parking across the street from the hotel, and we were able to store our bikes in a storage room behind...

Kelly

A modern kitchen with a central island, bar stools, and a dining table.

The Elmwood

Waterville

10/10 Excellent

Alma

A hotel room with a bed, a sofa, a desk, and a chair.

Fireside Inn & Suites Waterville

Waterville

10/10 Excellent

Benjamin

A Comfort Inn hotel with a covered entrance, multiple windows, and a brick facade.

Comfort Inn Augusta

Augusta

10/10 Excellent

I didn't expect to have such a great stay, given that the price was so low. Everyone there was very nice and helpful, especially Brenda working the breakfast room, and Peter at the front desk. The room was pretty big, I have two small children who had plenty of space to run around, and everyone really enjoyed their stay. Also the hotel is right next to the highway, so it's easy access. Plus the ninety nine restaurant just next door, and a mall about two minutes away.

Sebastien