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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Windsor vacation rentals

A living room with a fireplace, a glass of white wine, a cutting board with cheese, and a remote control.

1. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (115 reviews)
"Bigger than I expected and one of the homier properties I have been to in a while. Great location to walk around town and minutes to Augusta. Will book again"
United States
Shawn
The price is ￥19,005
￥31,509 total
includes taxes & fees
Nov 22 - Nov 23
High End Apartment in Downtown Hallowell
A cozy attic bedroom with wooden walls, a sloped ceiling, a TV, a bed, and a small kitchenette.

2. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is ￥14,374
￥32,554 total
includes taxes & fees
Nov 16 - Nov 17
Sister A-Frame in Woods B
An inflatable play structure with slides and tunnels.

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

Home Away From Home. Family friendly, comfortable- centrally located in Augusta
Augusta
The price is ￥24,436
￥38,473 total
includes taxes & fees
Nov 16 - Nov 17
Home Away From Home. Family friendly, comfortable- centrally located in Augusta
A modern kitchen with light green cabinets, a stainless steel microwave, and a wooden beam structure.

4. Two bedroom Mid Century Modern apartment in Downtown Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (98 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is ￥19,964
￥35,165 total
includes taxes & fees
Nov 22 - Nov 23
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A bedroom with a bed, a fireplace, a TV, a desk with a chair, and a kitchenette with a microwave.

5. The Lincoln Suite: historic king suite

The Lincoln Suite: historic king suite
Gardiner
The price is ￥21,561
￥25,590 total
includes taxes & fees
Nov 18 - Nov 19
The Lincoln Suite: historic king suite
A stone building with a central entrance, a flag, and a sign indicating 'ONE LINCOLN'.

6. The Oak Room: bright queen studio

The Oak Room: bright queen studio
Gardiner
The price is ￥21,561
￥24,372 total
includes taxes & fees
Nov 16 - Nov 17
The Oak Room: bright queen studio
Property grounds

7. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (50 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is ￥16,770
￥38,299 total
includes taxes & fees
Nov 16 - Nov 17
Central Maine Apartment offering 4 Seasons of Fun.
A wooden staircase with a clock, a kitchen area, and a living room with a sofa.

8. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (9 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
The price is ￥16,610
￥28,028 total
includes taxes & fees
Nov 17 - Nov 18
Cozy cottage in the Winthrop Lakes Area
A modern RV interior with a kitchen, seating area, and large windows.

9. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is ￥12,218
￥18,889 total
includes taxes & fees
Nov 30 - Dec 1
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

10. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
West Gardiner
9.8 out of 10, Exceptional, (23 reviews)
"This was the ideal Maine spot."
United States
Lisa W.
The price is ￥30,345
￥65,978 total
includes taxes & fees
Nov 19 - Nov 20
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A small blue cabin with a wooden deck and a porch, surrounded by trees.

11. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
Happy Cottage Near Everything 11
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

12. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Winthrop
9.2 out of 10, Wonderful, (5 reviews)
"Very nice property, great location, nice decor, pet friendly, and good kitchen area."
United States
Laura M.
The price is ￥27,949
￥45,087 total
includes taxes & fees
Nov 16 - Nov 17
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Property grounds

13. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Waldoboro
The price is ￥23,158
￥26,287 total
includes taxes & fees
Nov 16 - Nov 17
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A narrow hallway leading to a kitchen with wooden cabinets, a microwave, and a coffee maker.

14. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
The price is ￥25,234
￥37,254 total
includes taxes & fees
Nov 16 - Nov 17
Cozy House in the heart of Waterville Maine.
A wooden deck with Adirondack chairs and a fire pit overlooking a lake.

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

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
The price is ￥32,688
￥94,098 total
includes taxes & fees
Nov 16 - Nov 17
China Lake, Dog Friendly, Lots of space for family gatherings
A round above-ground pool with inflatable toys and a ladder.

16. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
The price is ￥18,367
￥35,862 total
includes taxes & fees
Nov 23 - Nov 24
The heart of the Belgrade Lakes
A spacious wooden interior with a dining area, kitchen, and bar.

17. Rustic Mountainside Cabin: “Liberty Lodge”

Rustic Mountainside Cabin: “Liberty Lodge”
Liberty
9.0 out of 10, Wonderful, (6 reviews)
"Place was great. Beautiful area and host was great about communicating so any questions we had were answered immediately"
United States
Brenda S.
The price is ￥24,436
￥81,646 total
includes taxes & fees
Nov 16 - Nov 17
Rustic Mountainside Cabin: “Liberty Lodge”
A stone building with a central entrance, a flag, and a sign indicating 'ONE LINCOLN'.

18. The Big Top: queen suite with a patio

The Big Top: queen suite with a patio
Gardiner
The price is ￥21,561
￥24,372 total
includes taxes & fees
Nov 16 - Nov 17
The Big Top: queen suite with a patio
A compact bedroom with a bed, a wooden wardrobe, a small cabinet, and a door with a number 5 sign.

19. The General's Quarters: bright king

The General's Quarters: bright king
Gardiner
The price is ￥21,561
￥24,372 total
includes taxes & fees
Nov 16 - Nov 17
The General's Quarters: bright king
A picnic table by a calm lake with trees in the background.

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

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
10.0 out of 10, Exceptional, (52 reviews)
"Enjoyed the property. The AC and laundry was great. Convenient for my purposes of visiting family. Calling was very helpful and responsive!"
United States
Jean D.
The price is ￥35,791
￥58,510 total
includes taxes & fees
Nov 16 - Nov 17
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Nice room. Well equipped. Very clean."
STEPHEN 1-night trip
Posted 14 hours ago
Fireside Inn & Suites Waterville

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

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 Wiscasset, Waterville and Farmington Railway Museum, or get outside and enjoy nature at Threemile Pond. In the larger area, you’ll find Capitol Park 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.