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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (113 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
$197 nightly
The price is $215
Nov 2 - Nov 3
Total with taxes and fees
High End Apartment in Downtown Hallowell
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

2. 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.
$165 nightly
The price is $180
Oct 12 - Oct 13
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A two-story house with a front porch, a small tree, and a brick pathway.

3. 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.
$252 nightly
The price is $275
Oct 13 - Oct 14
Total with taxes and fees
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.

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, (94 reviews)
"We keep coming back!!! The location is perfect! Walk to everything, eating, walking and watching sturgeonsThe apartment is so welcoming. Coffee options, bottled water…Looking forward to our next stay :)"
United States
Eileen S.
$220 nightly
The price is $240
Nov 1 - Nov 2
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A wooden cabin with a porch, a door, and a green chair.

5. 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.
$215 nightly
The price is $234
Nov 2 - Nov 3
Total with taxes and fees
Sister A-Frame in Woods B
A tent with a bed, two chairs, and a table.

6. Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (50 reviews)
"Wonderful place very peaceful very friendly Aaron was spectacular couldn't ask for a more wonderful enjoyable spot"
United States
Keith R
$140 nightly
The price is $153
Oct 7 - Oct 8
Total with taxes and fees
Get in touch with nature.
A covered porch with wicker furniture, a white door, and a welcome mat.

7. 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.
$169 nightly
The price is $184
Nov 1 - Nov 2
Total with taxes and fees
Cozy cottage in the Winthrop Lakes Area
Property grounds

8. 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.
$228 nightly
The price is $249
Oct 7 - Oct 8
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
A campsite with a white chair, a black tarp, and a pile of branches.

9. Glamping in the Lake - Ovah to Camp!

Glamping in the Lake - Ovah to Camp!
Manchester
$204 nightly
The price is $222
Oct 7 - Oct 8
Total with taxes and fees
Glamping in the Lake - Ovah to Camp!
A wooden pathway leading to a body of water, surrounded by dense greenery.

10. Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly

Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Monmouth
10.0 out of 10, Exceptional, (4 reviews)
"The island is great from the walking trails, amenities and great fishing. "
United States
Jeremy F.
$159 nightly
The price is $173
Oct 7 - Oct 8
Total with taxes and fees
Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
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.

11. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (63 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.
$235 nightly
The price is $256
Oct 15 - Oct 16
Total with taxes and fees
Cozy House in the heart of Waterville Maine.
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

12. 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
$215 nightly
The price is $234
Oct 7 - Oct 8
Total with taxes and fees
The heart of the Belgrade Lakes
A campfire surrounded by rocks and two wooden Adirondack chairs.

13. Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
9.0 out of 10, Wonderful, (7 reviews)
"Very quite and private and beautiful surroundings"
United States
Gary
$149 nightly
The price is $162
Oct 7 - Oct 8
Total with taxes and fees
Glamping at Maine Water Buffalo Farm
Outdoor dining

14. 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
$166 nightly
The price is $181
Oct 7 - Oct 8
Total with taxes and fees
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

15. 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, (21 reviews)
"Great property with two showers and two bathrooms Great location in Gardiner"
United States
Robert M.
$400 nightly
The price is $436
Oct 20 - Oct 21
Total with taxes and fees
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.

16. Rustic Mountainside Cabin: “Liberty Lodge”

Rustic Mountainside Cabin: “Liberty Lodge”
Liberty
9.6 out of 10, Exceptional, (5 reviews)
$537 nightly
The price is $586
Oct 7 - Oct 8
Total with taxes and fees
Rustic Mountainside Cabin: “Liberty Lodge”
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

17. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (19 reviews)
"Great communication. The location was excellent for a few day trips. Very clean and well maintained. Would definitely stay here again if in the area."
United States
Patricia
$207 nightly
The price is $226
Oct 7 - Oct 8
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
A wooden deck with a glass door leading to a room.

18. 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
$220 nightly
The price is $223
Oct 7 - Oct 8
Total with taxes and fees
Tiny Cottage Near Everything 10
A floating house with a glass door, a deck, and a table and chairs.

19. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (12 reviews)
"What an absolute pleasure it was staying in the floating home on the island. It was everything we wanted it to be. We will make this an annual trip. "
United States
Carissa P.
$224 nightly
The price is $244
Oct 12 - Oct 13
Total with taxes and fees
Floating Island Cabin
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

Budget Host Airport Inn

Budget Host Airport Inn

10/10 Excellent
"Breakfast was bare minimum but price was right. Front desk clerk was nice."
Brenda 1-night trip
Posted less than an hour ago
Budget Host Airport Inn

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $181 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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 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.