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Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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 CA $170
CA $282 total
includes taxes & fees
Nov 22 - Nov 23
High End Apartment in Downtown Hallowell

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 CA $128
CA $291 total
includes taxes & fees
Nov 16 - Nov 17
Sister A-Frame in Woods B

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 CA $218
CA $344 total
includes taxes & fees
Nov 16 - Nov 17
Home Away From Home. Family friendly, comfortable- centrally located in Augusta

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 CA $178
CA $314 total
includes taxes & fees
Nov 22 - Nov 23
Two bedroom Mid Century Modern apartment in Downtown Hallowell

5. The Lincoln Suite: historic king suite

The Lincoln Suite: historic king suite
Gardiner
The price is CA $193
CA $229 total
includes taxes & fees
Nov 18 - Nov 19
The Lincoln Suite: historic king suite

6. The Oak Room: bright queen studio

The Oak Room: bright queen studio
Gardiner
The price is CA $193
CA $218 total
includes taxes & fees
Nov 16 - Nov 17
The Oak Room: bright queen studio

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 CA $150
CA $342 total
includes taxes & fees
Nov 16 - Nov 17
Central Maine Apartment offering 4 Seasons of Fun.

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 CA $148
CA $252 total
includes taxes & fees
Nov 17 - Nov 18
Cozy cottage in the Winthrop Lakes Area

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 CA $109
CA $169 total
includes taxes & fees
Nov 30 - Dec 1
Fabulous 3-bedroom RV with direct access to the Sebasticook River!

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 CA $271
CA $590 total
includes taxes & fees
Nov 19 - Nov 20
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

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

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 CA $250
CA $403 total
includes taxes & fees
Nov 16 - Nov 17
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

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 CA $207
CA $235 total
includes taxes & fees
Nov 16 - Nov 17
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

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 CA $225
CA $333 total
includes taxes & fees
Nov 16 - Nov 17
Cozy House in the heart of Waterville Maine.

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 CA $292
CA $841 total
includes taxes & fees
Nov 16 - Nov 17
China Lake, Dog Friendly, Lots of space for family gatherings

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 CA $164
CA $322 total
includes taxes & fees
Nov 23 - Nov 24
The heart of the Belgrade Lakes

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 CA $218
CA $730 total
includes taxes & fees
Nov 16 - Nov 17
Rustic Mountainside Cabin: “Liberty Lodge”

18. The Big Top: queen suite with a patio

The Big Top: queen suite with a patio
Gardiner
The price is CA $193
CA $218 total
includes taxes & fees
Nov 16 - Nov 17
The Big Top: queen suite with a patio

19. The General's Quarters: bright king

The General's Quarters: bright king
Gardiner
The price is CA $193
CA $218 total
includes taxes & fees
Nov 16 - Nov 17
The General's Quarters: bright king

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 CA $320
CA $523 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

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 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.