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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Windsor holiday rentals

A living room with a fireplace, a television, and a sofa.

1. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (114 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 £145
includes taxes & fees
19 Nov - 20 Nov
High End Apartment in Downtown Hallowell
A wooden cabin with a porch, a door, and a green chair.

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 £157
includes taxes & fees
10 Nov - 11 Nov
Sister A-Frame in Woods B
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

3. 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, (96 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is £162
includes taxes & fees
10 Nov - 11 Nov
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A wooden cabin with a porch, a rocking chair, and a table with a lantern.

4. Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin
Monmouth
10.0 out of 10, Exceptional, (13 reviews)
"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....
United States
Peter O.
The price is £221
includes taxes & fees
8 Nov - 9 Nov
Naughty Dog Private Island Log Cabin
A wooden deck with a railing and steps leading to a house.

5. 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 £234
includes taxes & fees
10 Nov - 11 Nov
Home Away From Home. Family friendly, comfortable- centrally located in Augusta
A covered porch with wicker furniture, a white door, and a welcome mat.

6. 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 £132
includes taxes & fees
16 Nov - 17 Nov
Cozy cottage in the Winthrop Lakes Area
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 £178
includes taxes & fees
8 Nov - 9 Nov
Central Maine Apartment offering 4 Seasons of Fun.
A wooden interior with a radial wooden ceiling design and a central skylight.

8. Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (11 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
The price is £171
includes taxes & fees
8 Nov - 9 Nov
Island Tree House Glamping
A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

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)
"Everything was so clean and nice!! Beautiful spot! Had everything we needed for our stay! Host was responsive to questions. Would come again for sure!!!"
United States
Hannah
The price is £90
includes taxes & fees
30 Nov - 1 Dec
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

10. 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 £160
includes taxes & fees
16 Nov - 17 Nov
The heart of the Belgrade Lakes
Outdoor dining

11. 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 £129
includes taxes & fees
6 Nov - 7 Nov
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
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.

12. 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 £183
includes taxes & fees
10 Nov - 11 Nov
Cozy House in the heart of Waterville Maine.
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

13. 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 £298
includes taxes & fees
10 Nov - 11 Nov
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A spacious wooden cabin with a cozy living area featuring a sofa, a coffee table, and a fireplace.

14. 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 £412
includes taxes & fees
2 Dec - 3 Dec
Rustic Mountainside Cabin: “Liberty Lodge”
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

15. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is £157
includes taxes & fees
9 Nov - 10 Nov
Cheerful Cottage with Loft 9
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

16. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is £147
includes taxes & fees
9 Nov - 10 Nov
Spacious 1 Bedroom Cottage Close to Everything 5
A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

17. 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
The price is £130
includes taxes & fees
9 Nov - 10 Nov
Happy Cottage Near Everything 11
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

18. 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
9.0 out of 10, Wonderful, (4 reviews)
"Very nice property, great location, nice decor, pet friendly, and good kitchen area."
United States
Laura M.
The price is £220
includes taxes & fees
8 Nov - 9 Nov
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

19. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 reviews)
"The cabin was perfect for our two night stay. It was very clean and it felt just like being at home. Misty was a responsive host and I would definitely rent here again."
United States
Tonilynne D.
The price is £101
includes taxes & fees
19 Nov - 20 Nov
Charming cabin in the birches right on the atv trail!
A cozy interior of a geodesic dome tent with a bed, a sofa, a small table with a bottle, a fireplace, and a view of the outdoors.

20. Come Spring Farm Glamping Dome 2

Come Spring Farm Glamping Dome 2
Union
5.6 out of 10, (4 reviews)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
United States
Healy C.
The price is £154
includes taxes & fees
6 Nov - 7 Nov
Come Spring Farm Glamping Dome 2
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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Find holiday rentals that suit your style

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Top Windsor Hotel Reviews

A reception desk with a "Welcome to the Lobster State" sign, a wooden panel design, and a "Hilton" logo.
Hampton Inn Augusta

Hampton Inn Augusta

Hampton Inn Augusta
Augusta

10/10 Excellent

Excellent, highly recomended
United Kingdom
Paul
Reviewed October 7, 2023
Hampton Inn Augusta

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as £89 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select 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 holiday rentals that Windsor has to offer?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area, you’ll find Capitol Park and Maine State House.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.