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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor vacation rentals

TV

1. 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, (92 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
$209 nightly
The price is $227
Sep 3 - Sep 4
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Terrace/patio

2. Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (45 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
Sep 2 - Sep 3
Total with taxes and fees
Get in touch with nature.
Interior

3. 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.
$160 nightly
The price is $175
Sep 8 - Sep 9
Total with taxes and fees
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
TV, fireplace, books

4. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
$305 nightly
The price is $332
Sep 16 - Sep 17
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
Property grounds

5. Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (22 reviews)
"Great location for visiting the coast."
United States
Sallie S.
$368 nightly
The price is $401
Sep 3 - Sep 4
Total with taxes and fees
Rustic Retreat Across from Lake; Family Friendly!
Exterior

6. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (4 reviews)
"I’ve stayed in many rental properties and this one is by far the cleanest and nicest. Everything was exactly as described and there was even a second ac unit in the bedroom. It’s on a nice quiet street and convenient to many things. You truly can’t go wrong choosing to stay here."
United States
Lisa G.
$257 nightly
The price is $280
Sep 2 - Sep 3
Total with taxes and fees
Perfectly Located 1 Bedroom, newly remodeled
Exterior

7. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$241 nightly
The price is $262
Sep 3 - Sep 4
Total with taxes and fees
Sister A-Frame in Woods B
Interior

8. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (109 reviews)
"Lovely stay in Hallowell."
United States
Lori D.
$186 nightly
The price is $203
Sep 13 - Sep 14
Total with taxes and fees
High End Apartment in Downtown Hallowell
House (3 Bedrooms) | Front of property

9. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
$450 nightly
The price is $491
Sep 9 - Sep 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Property grounds

10. Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
8.8 out of 10, Excellent, (6 reviews)
"Very quite and private and beautiful surroundings"
United States
Gary
$149 nightly
The price is $162
Sep 2 - Sep 3
Total with taxes and fees
Glamping at Maine Water Buffalo Farm
Interior

11. Island Tree House Glamping

Island Tree House Glamping
Monmouth
9.8 out of 10, Exceptional, (10 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
$238 nightly
The price is $259
Sep 3 - Sep 4
Total with taxes and fees
Island Tree House Glamping
Interior

12. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
$130 nightly
The price is $142
Sep 7 - Sep 8
Total with taxes and fees
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Terrace/patio

13. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (7 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
$177 nightly
The price is $192
Sep 10 - Sep 11
Total with taxes and fees
Cozy cottage in the Winthrop Lakes Area
Interior

14. Quiet & Lovely Lakefront Cottage for Families!

Quiet & Lovely Lakefront Cottage for Families!
Union
9.8 out of 10, Exceptional, (16 reviews)
"Evocative of my youth and going to the family lake camp in the summer. We had great weather and a great time. The cabin is a ‘Mainer’s’ memories wrapped in eclectic reminders. What a joy!"
United States
Venise B.
$468 nightly
The price is $510
Sep 7 - Sep 8
Total with taxes and fees
Quiet & Lovely Lakefront Cottage for Families!
Property grounds

15. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (9 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.
$203 nightly
The price is $221
Sep 16 - Sep 17
Total with taxes and fees
Floating Island Cabin
Coffee/tea maker, fridge, microwave, stovetop

16. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"It was a wonderful stay at this home. The home was incredibly clean, the beds were very comfortable and had great bedding on them. It was a great location to all the nearby places we wanted to go to. Loved the historic charm. We would love to come and stay again!"
United States
Tina S.
$461 nightly
The price is $502
Sep 9 - Sep 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Smart TV, fireplace, books

17. Rustic Mountainside Cabin: “Liberty Lodge”

Rustic Mountainside Cabin: “Liberty Lodge”
Liberty
10.0 out of 10, Exceptional, (3 reviews)
"Place was great. Beautiful area and host was great about communicating so any questions we had were answered immediately"
United States
Brenda S.
$583 nightly
The price is $635
Sep 22 - Sep 23
Total with taxes and fees
Rustic Mountainside Cabin: “Liberty Lodge”
2 bedrooms, WiFi, bed sheets

18. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
$210 nightly
The price is $229
Sep 3 - Sep 4
Total with taxes and fees
The heart of the Belgrade Lakes
Cottage (2 Bedrooms) | Front of property

19. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
$298 nightly
The price is $324
Sep 16 - Sep 17
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Clean and friendly staff!"
Lisa 2-night trip
Posted less than an hour ago
Fireside Inn & Suites Waterville

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 $142 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 Maine State Museum, or get outside and enjoy nature at Threemile Pond. In the larger area, you’ll find China Lake and Old Fort Western.

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.