Windsor Vacation Rentals

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Nov 10 - Nov 11
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Nov 11 - Nov 12
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Windsor

TV
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Sidney
9.8 out of 10, Exceptional, (34)
"The house was very clean, well equipped, great location! Owner was super nice and easy going. I brought my all stars team down to play little Fenway and will absolutely try to get this house again if we ever come back. "
United States
Alicia G.
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Property grounds
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Nobleboro
10.0 out of 10, Exceptional, (42)
"This a gem of a place. Quiet, cozy spots, beautiful proximity to the lake. We really enjoyed our night, and were sorry we did not have a longer stay."
United States
Sarah H.
$268 nightly
The price is $292
Nov 13 - Nov 14
Total with taxes and fees
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.8 out of 10, Excellent, (17)
"Perfect old fashion Maine cottage! Great sunsets!"
United States
Anita W.
$293 nightly
The price is $319
Nov 12 - Nov 13
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
Fridge, microwave, oven, stovetop
Lakefront Cabin

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"Beautiful location, lovely cabin. Ken was very responsive and helpful. Fun rustic cabin."
United States
Anni D.
Lakefront Cabin
Fridge, microwave, oven, stovetop
Waterfront 2br/2ba cottage

Waterfront 2br/2ba cottage

West Gardiner
9.8 out of 10, Exceptional, (15)
"Very nice and clean place. We used this rental as a hub to go around and see lots that Maine had to offer. Hosts were very nice and kept a very clean place."
United States
Bruce J.
$297 nightly
The price is $323
Nov 12 - Nov 13
Total with taxes and fees
Waterfront 2br/2ba cottage
TV, fireplace
Peaceful home with forest views & great yard - minutes to town

Peaceful home with forest views & great yard - minutes to town

Wiscasset
7.8 out of 10, Good, (9)
"Your home is beautiful!! Love all the windows, very comfortable!!"
United States
Sharon T.
Peaceful home with forest views & great yard - minutes to town
Outdoor dining
Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Rome
9.8 out of 10, Exceptional, (19)
"The stay was a very nice place and we will be coming back with the whole family next time. "
United States
Al Q.
Cozy Long Pond Cottage: private mooring & shared dock
Dining
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Albion
9.8 out of 10, Exceptional, (37)
"Cute house with deck overlooking the pond with almost daily sightings of eagles, loons and ducks. We loved it here and would stay here again if we come back this way again. I hated to leave this cute home. "
United States
stehpen g.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Smart TV
Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.

Waterville
9.6 out of 10, Exceptional, (48)
"Charming interior design, modern conveniences and super clean!"
United States
Marc M.
Cozy House in the heart of Waterville Maine.
Property grounds
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
Readfield
10.0 out of 10, Exceptional, (7)
"It was a wonderful week. The cabin is very well appointed. We lacked for nothing! Thank you "
United States
Gigi A.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Outdoor spa tub
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Manchester
10.0 out of 10, Exceptional, (253)
"Spacious, clean comfortable. Beautiful views. Right on lake."
United States
V H.
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly
Terrace/patio
Get in touch with nature.

Get in touch with nature.

Richmond
10.0 out of 10, Exceptional, (35)
"Such a great experience! Everything was clean and better than we imagined! Aaron sent videos on how to run everything right before our arrival. We loved the outdoor shower, comfy bed & having a variety of games to play. Such a beautiful property! "
United States
Amanda B.
Get in touch with nature.
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (7)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Nov 12 - Nov 13
Total with taxes and fees
Sister A-Frame in Woods B
Fridge, microwave, oven, stovetop
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Mount Vernon
10.0 out of 10, Exceptional, (20)
"Easy 5/5 rating. The most peaceful week in Maine thanks to this house, lake and gorgeous back deck. We could not have had a better experience. Cannot recommend this place enough! "
United States
Alexandria K.
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Interior
NEW! Long Pond Lake View Getaway w/HOT TUB, ME

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Mount Vernon
10.0 out of 10, Exceptional, (2)
"This clean and spacious home is the perfect spot for a family getaway. It is well stocked, and the bed are very comfortable. We loved it!"
United States
Patricia W.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME
Exterior
Nature lovers Paradise your own island

Nature lovers Paradise your own island

West Gardiner
9.8 out of 10, Exceptional, (70)
"Amazing property! "
United States
Emily H.
Nature lovers Paradise your own island
Fridge, microwave, oven, stovetop
Kayakers’ Cabin- “Maine Cabin Masters” remodel.

Kayakers’ Cabin- “Maine Cabin Masters” remodel.

Newcastle
10.0 out of 10, Exceptional, (54)
"Weather didn't cooperate much but we enjoyed our time nonetheless. Love this spot for it's proximity to the village of Damariscotta. So convenient and a cute place to stay."
United States
Kimberly G.
Kayakers’ Cabin- “Maine Cabin Masters” remodel.
Property grounds
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
9.6 out of 10, Exceptional, (85)
"The property was spacious for our group of 7. Plenty of room for kids to stretch out and enjoy. The fire pit was nice for our s’mores night and the sunsets topped it off. Laundry on site is a bonus. Not too much room for pantry items but we made it work. Overall we were pleased. "
United States
Donna W.
Private and Calming Waterfront to the Rescue!
Exterior
Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm

Union
9.6 out of 10, Exceptional, (17)
"I stayed here with my mom, and it was a fun experience. We loved the animals the sheep, goats, and alpacas. The lounge area was nice too. Our dome was very cool, the beds comfortable, it was a bit cool in there to walk around but we were warm at night. The only negative was the housekeeping could have been better."
United States
Rebecca
Dome 1 - Luxury Dome at Come Spring Farm
Exterior
Charming Guest House on Farm - Pets Welcome

Charming Guest House on Farm - Pets Welcome

Oakland
10.0 out of 10, Exceptional, (7)
"The farmhouse was clean and charming. The kitchen was well-stocked. Kathleen was an excellent communicator. She went out of her way to make sure we were comfortable— including making a bonfire for smores! We loved getting to be with her sweet kitties and amazing donkeys, mule, and horse."
United States
amy C.
$249 nightly
The price is $267
Nov 12 - Nov 13
Total with taxes and fees
Charming Guest House on Farm - Pets Welcome
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Staff was excellent, and the property was in a great shape"
Daniel J. 1-night trip
Posted 1 day ago
Maine Evergreen Hotel, an Ascend Collection Hotel

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 $228 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.

Explore a world of travel with Expedia

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?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: This vacation home rental outside of Windsor is located in a rural location and has a hot tub, a barbecue grill, and air-conditioning 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.

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 Capitol Park. In the larger area, you’ll find Old Fort Western 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.