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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windsor holiday rentals

A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

1. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (2 reviews)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
The price is HK$1,095
HK$1,364 total
includes taxes & fees
26 Oct - 27 Oct
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A living room with a fireplace, a glass of white wine, a cutting board with cheese, and a remote control.

2. 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 HK$855
HK$1,583 total
includes taxes & fees
3 Nov - 4 Nov
High End Apartment in Downtown Hallowell
A wooden cabin with a porch, a door, and a green chair.

3. 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 HK$706
HK$1,736 total
includes taxes & fees
3 Nov - 4 Nov
Sister A-Frame in Woods B
A two-story house with a front porch, a small tree, and a brick pathway.

4. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (6 reviews)
"The area is so convenient for any business you have in the Augusta area- right off the main thoroughfare yet far enough away to be private. Check in was as simple as getting the lock code from vrbo check in emails. The apartment is even more lovely than the pictures- almost too clean and comfortable to be real! Bedtime was silent so I got a great night sleep. I only wish we would have had more time to enjoy :) Highly recommend!! "
United States
w c.
The price is HK$1,264
HK$2,181 total
includes taxes & fees
21 Oct - 22 Oct
Perfectly Located 1 Bedroom, newly remodeled
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

5. 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, (94 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is HK$981
HK$1,882 total
includes taxes & fees
1 Nov - 2 Nov
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

6. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"It was amazing! Shawna was great! I forgot to add our pet on the original booking and she was so responsive and we got everything sorted out. The apartment was so comfortable and decorated beautifully! Great space from kids room with things to entertain them to calm adult bedroom. The kitchen was well stocked and had everything you could think of. We loved “the fluffy butt hut” chicken coop!!! This is a dream place, from veggie garden, pool, tree house, chicken coop. Love it! Will definitely...
United States
Tri C.
The price is HK$903
HK$1,839 total
includes taxes & fees
22 Oct - 23 Oct
The heart of the Belgrade Lakes
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

7. 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, (22 reviews)
"This was the ideal Maine spot."
United States
Lisa W.
The price is HK$1,417
HK$3,306 total
includes taxes & fees
21 Oct - 22 Oct
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A wooden deck with a glass door leading to a room.

8. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is HK$714
HK$1,691 total
includes taxes & fees
21 Oct - 22 Oct
Tiny Cottage Near Everything 10
A living room with a fireplace, a mounted TV, and bookshelves filled with books.

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

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
10.0 out of 10, Exceptional, (51 reviews)
"We loved everything about this place! It’s beautifully decorated and feels like a home away from away. The host was wonderful and made it easy to communicate with her. The view from the deck is so pretty! I loved having a cup of tea out there and looking at the water. It was a perfect spot! We are so grateful!"
United States
Rhiannon A.
The price is HK$1,441
HK$2,777 total
includes taxes & fees
21 Oct - 22 Oct
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
A covered porch with wicker furniture, a white door, and a welcome mat.

10. 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 HK$816
HK$1,446 total
includes taxes & fees
1 Nov - 2 Nov
Cozy cottage in the Winthrop Lakes Area
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 HK$1,138
HK$1,420 total
includes taxes & fees
21 Oct - 22 Oct
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Property grounds

12. 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 HK$816
HK$1,942 total
includes taxes & fees
1 Nov - 2 Nov
Central Maine Apartment offering 4 Seasons of Fun.
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

13. 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)
"We will miss this house and would be happy to come back again. The ac in every bedroom plus the main floor made the most humid days comfortable. And China Lake is a wonderful place to have a piece of to yourself."
United States
Lisa J.
The price is HK$1,639
HK$3,967 total
includes taxes & fees
21 Oct - 22 Oct
China Lake, Dog Friendly, Lots of space for family gatherings
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.

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)
"Less than 5 minutes to Colby. We were there for a camp. AC in both bedrooms. Nice artwork and decor."
United States
Leslie G.
The price is HK$1,161
HK$1,993 total
includes taxes & fees
3 Nov - 4 Nov
Cozy House in the heart of Waterville Maine.
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

15. 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 HK$1,373
HK$2,429 total
includes taxes & fees
21 Oct - 22 Oct
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A wooden cabin with a porch, a rocking chair, and a table with a lantern.

16. 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 HK$730
HK$2,763 total
includes taxes & fees
1 Nov - 2 Nov
Naughty Dog Private Island Log Cabin
A wooden interior with a radial wooden ceiling design and a central skylight.

17. 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 HK$86
HK$1,737 total
includes taxes & fees
28 Oct - 29 Oct
Island Tree House Glamping
A bedroom with a bed, a bedside table, and a window with curtains.

18. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (12 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is HK$1,138
HK$1,420 total
includes taxes & fees
21 Oct - 22 Oct
Peaceful Intown Studio ~ Walk to Shops & Dining
A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

19. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.4 out of 10, Very good, (5 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is HK$1,295
HK$2,010 total
includes taxes & fees
21 Oct - 22 Oct
Come Spring Farm Airstream , Lake & farm animals
A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

20. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.8 out of 10, Excellent, (16 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is HK$1,295
HK$1,886 total
includes taxes & fees
2 Nov - 3 Nov
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
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

Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

10/10 Excellent
"Check in was quick. Staff was friendly and helpful. Room was clean. TV excellent. Breakfast was good. Checked out while we grabbed breakfast. Loved this place."
Keith 2-night trip
Posted 2 hours ago
Cod Cove Inn, BW Signature Collection

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:

  • View our selection of featured holiday rentals in Windsor
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  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

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

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.