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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 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, (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
The price is CA $168
CA $302 total
includes taxes & fees
Nov 8 - Nov 9
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.
The price is CA $198
CA $247 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is CA $228
CA $399 total
includes taxes & fees
Oct 22 - Oct 23
Perfectly Located 1 Bedroom, newly remodeled
A wooden cabin with a porch, a door, and a green chair.

4. 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 $141
CA $334 total
includes taxes & fees
Nov 3 - Nov 4
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.

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 CA $177
CA $344 total
includes taxes & fees
Nov 1 - Nov 2
Two bedroom Mid Century Modern apartment in Downtown Hallowell
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, (52 reviews)
"Perfect place to reset your soul! Loved it!"
United States
Vincent
The price is CA $153
CA $244 total
includes taxes & fees
Oct 18 - Oct 19
Get in touch with nature.
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

7. 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 CA $163
CA $331 total
includes taxes & fees
Oct 18 - Oct 19
The heart of the Belgrade Lakes
A covered porch with wicker furniture, a white door, and a welcome mat.

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 $147
CA $260 total
includes taxes & fees
Nov 2 - Nov 3
Cozy cottage in the Winthrop Lakes Area
Outdoor dining

9. 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 $205
CA $256 total
includes taxes & fees
Oct 19 - Oct 20
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Property grounds

10. 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 $147
CA $351 total
includes taxes & fees
Nov 5 - Nov 6
Central Maine Apartment offering 4 Seasons of Fun.
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

11. 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 CA $269
CA $617 total
includes taxes & fees
Oct 29 - Oct 30
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A wooden deck with a glass door leading to a room.

12. 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 CA $123
CA $294 total
includes taxes & fees
Oct 20 - Oct 21
Tiny Cottage Near Everything 10
A spacious wooden cabin with a cozy living area featuring a sofa, a coffee table, and a fireplace.

13. Rustic Mountainside Cabin: “Liberty Lodge”

Rustic Mountainside Cabin: “Liberty Lodge”
Liberty
9.6 out of 10, Exceptional, (5 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 $233
CA $820 total
includes taxes & fees
Oct 29 - Oct 30
Rustic Mountainside Cabin: “Liberty Lodge”
A wooden interior with a radial wooden ceiling design and a central skylight.

14. 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 CA $16
CA $319 total
includes taxes & fees
Oct 28 - Oct 29
Island Tree House Glamping
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

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)
"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 CA $291
CA $707 total
includes taxes & fees
Oct 18 - Oct 19
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.

16. 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 CA $209
CA $364 total
includes taxes & fees
Nov 2 - Nov 3
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.

17. 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 CA $247
CA $435 total
includes taxes & fees
Oct 21 - Oct 22
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A living room with a fireplace, a mounted TV, and bookshelves filled with books.

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

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (50 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 CA $317
CA $572 total
includes taxes & fees
Oct 19 - Oct 20
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

19. 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 CA $132
CA $317 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 1 Bedroom Cottage Close to Everything 5
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

The Elmwood

The Elmwood

8/10 Good
"Very clean hotel. Nice array of food for breakfast A little too close to the highway for me"
Stefanie 1-night trip
Posted 10 hours ago
The Elmwood

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $362 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 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.