Windsor Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Windsor

A Charming Waterfront Cottage with Touches of Elegance
10.0 out of 10, Exceptional, 78 reviews
"We had a wonderful stay. The porch had amazing views and was comfortable even in the winter. The kitchen was large and incredibly well equipped. The cottage was beautifully decorated and had lots of natural light."
A Charming Waterfront Cottage with Touches of Elegance
Waterfront 2br/2ba cottage
10.0 out of 10, Exceptional, 3 reviews
"Great location. Clean. Very well stocked. Great communication."
The price is CA $301
CA $662 total
includes taxes & fees
Jun 3 - Jun 4
Waterfront 2br/2ba cottage
Beautiful Midcoast Maine Condominium with inground pool
9.4 out of 10, Exceptional, 30 reviews
"Great location"
The price is CA $192
CA $324 total
includes taxes & fees
Jun 3 - Jun 4
Beautiful Midcoast Maine Condominium with inground pool
Save an average of 15% on thousands of hotels when you're signed in
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
8.4 out of 10, Very good, 6 reviews
"Myself and 4 friends booked this home on the water for an annual super bowl ice fishing trip. The house was just as described, spacious and comfortable. The pond is beautiful and the fishing was outstanding, we caught fish all day long. Location is good as well, with plenty of restaurants and downtown Augusta within 10 to 15 minutes. Great home for the price."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok
7.8 out of 10, Good, 10 reviews
"The house and surrounding were very nice. Exactly as described and had some nice touches left by the management company- extra soap, laundry pods, doggie poop bags. The only concerns were that the keypad on the door was temperamental and didn’t work our entire visit (thankfully there was a key in a lockbox so we could get inside when it was cold and raining) and there were several dishes put away dirty. Overall it was a great property that we hope to return to in warmer weather and enjoy the...
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
9.8 out of 10, Exceptional, 20 reviews
"I was offered Stella which is a beautiful little apartment due to a mistake I made when applying to stay in Roxie. I didn't realize Roxie was solar and I really needed electricity for this stay. It was a more a business trip not a camping trip.Sherri very graciously let me stay in Stella which was wonderful . Very clean, bright , everything you could need . I would definitely stay there again.."
The price is CA $130
CA $216 total
includes taxes & fees
Jun 3 - Jun 4
Tiny House on 100 Acres Kayaks/Canoes/Paddleboards
Lakefront cottage with dock, screened porch, & Island in Biscay Pond
8.8 out of 10, Excellent, 13 reviews
"This is the perfect Maine camp! Clean, comfortable and cute."
Lakefront cottage with dock, screened porch, & Island in Biscay Pond
Sunset Chalet- Stylish Waterfront Gem
10.0 out of 10, Exceptional, 20 reviews
"This is by far one of the best places we’ve stayed. From the beautiful decor, exposed wood and cozy fireplace. It was the attention to detail and small little extras that made this an extra special visit. The serene music playing as you enter the home to the specialized note and picnic basket! They are very accommodating to any situation that may arise and communicate on a five star level. An amazing stay and will be visiting again!"
The price is CA $655
CA $1,217 total
includes taxes & fees
Jun 3 - Jun 4
Sunset Chalet- Stylish Waterfront Gem
An off-grid comfy cabin in a quiet corner of a midcoast organic farm
10.0 out of 10, Exceptional, 21 reviews
"The cabin was absolutely wonderful. It was a great "home-base" for my husband and I. We slept great. I really enjoyed using the kerosene lamps and the woodburning stove. I would absolutely recommend it."
An off-grid comfy cabin in a quiet corner of a midcoast organic farm
Rustic Retreat Across from Lake; Family Friendly!
8.4 out of 10, Very good, 9 reviews
"This property is very charming and was the perfect quiet location for a weekend away. The place was clean and quiet and had beautiful views of the lake! Recommend for sure!"
Rustic Retreat Across from Lake; Family Friendly!
MoonLight Treehouse- Luxury Waterfront Escape
10.0 out of 10, Exceptional, 10 reviews
"My husband and I have 4 kids together and 7 pets, to say we needed this little trip is an understatement. It was peaceful, beautiful and so relaxing."
The price is CA $591
CA $1,139 total
includes taxes & fees
Jun 3 - Jun 4
MoonLight Treehouse- Luxury Waterfront Escape
Get in touch with nature.
10.0 out of 10, Exceptional, 9 reviews
"Great property very private will be back very soon"
The price is CA $137
CA $224 total
includes taxes & fees
Jun 3 - Jun 4
Get in touch with nature.
Steps to Your Private 100 Feet of Lake Front - $800/Week
8.6 out of 10, Excellent, 13 reviews
"It was very difficult for me to be in the situation with no Internet and much too far to drive into town every time I needed it. I also didn’t realize that he didn’t supply linens and towels so well though the location was gorgeous those were too big problems for me I really don’t know if I mentioned that on the online booking but I was taken by surprise. The place was a little funky for my taste"
Steps to Your Private 100 Feet of Lake Front - $800/Week
Remodeled Waterfront Home with Wraparound Deck, Water Views, & Beach Access
9.0 out of 10, Wonderful, 32 reviews
"PROS: We spent eight nights in this modern up-to-date home. After a couple of fits and starts regarding check-in everything went smoothly. The location, while slightly remote, is still only a 15 minute trip to Damariscotta where you will find plenty of restaurants, shopping and even a theater. The large deck and water views were a plus. Happy to see that a railing had been added to the stairway leading to the main bedroom. CONS: Climate change has made the old adage that you don't need A/C in...
Remodeled Waterfront Home with Wraparound Deck, Water Views, & Beach Access
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
10.0 out of 10, Exceptional, 23 reviews
"Lovely little house right on Annabessacook Lake in Maine, with everything you might need. Great kayaking right from the property. Thoroughly enjoyed our stay."
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Nature lovers Paradise your own island
9.8 out of 10, Exceptional, 59 reviews
"This is our third summer staying here for a week and it was perfect as usual! Thanks Deb!"
Nature lovers Paradise your own island
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, 42 reviews
"The picture you show was the owners 1st property and we could not access the property with my elderly family. When I called the owner, he offered me a second option of another property. That is the property I rated. It was very kind of the owner to accomodate us. It was a lit more driving than we intended but the accommodstions were much better for us."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Dog-friendly waterfront home on Crawford Pond with dock, deck & great view
Dog-friendly waterfront home on Crawford Pond with dock, deck & great view
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
7.6 out of 10, Good, 22 reviews
"The location of King’s Kastle on Salmon Lake is excellent. The lake is wide at that point and offers great views of the sunrise, particularly from the upstairs master bedroom suite. The lake has less development than others where we have stayed in Maine. We enjoyed seeing loons, eagles, and osprey which are abundant. We went in the latter part of August when the kids’ summer camps had closed, which reduced boat traffic. The cottage is roomy and has a long list of amenities. All appliances were...
Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks
Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok
9.0 out of 10, Wonderful, 14 reviews
"House was clean and cozy. We stayed for a yearly ice fishing trip, caught fish and enjoyed the experience."
Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok
Don't see what you're looking for?
See all available properties in Windsor
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.

Windsor Vacation Rental Travel Info

Other types of properties in Windsor you may be interested in

Senator Inn & Spa
3.0 star property
7.8 out of 10, Good, 1,001 reviews
"Look the breakfast "
The price is CA $265
CA $304 total
includes taxes & fees
Jun 17 - Jun 18
Senator Inn & Spa
Maine Evergreen Hotel, Ascend Hotel Collection
2.5 star property
9.2 out of 10, Wonderful, 1,002 reviews
"We enjoyed the quaintness of the inn. It was fun yo view sll of the artwork. . Everyone who worked there that we encountered was great!"
The price is CA $226
CA $247 total
includes taxes & fees
Jun 2 - Jun 3
Maine Evergreen Hotel, Ascend Hotel Collection
Best Western Plus Waterville Grand Hotel
3.0 star property
7.4 out of 10, Good, 848 reviews
"Very nice room."
The price is CA $223
CA $243 total
includes taxes & fees
Jun 13 - Jun 14
Best Western Plus Waterville Grand Hotel
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.

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 $130 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?

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!: This vacation home rental outside of Windsor is situated on the beach and has a patio and a barbecue grill to help you feel content during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of books.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Samantha Smith, or get outside and enjoy nature at Kennebec River Rail Trail. In the larger area, you’ll find Old Fort Western and Capitol Park.

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.

Recent reviews of Windsor properties
Expedia verified reviews