Windsor Holiday Rentals

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Holiday Rentals in Windsor

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (61)
"Great family camp right on the water with great views and paddle boats to play and fish the lake. Nice host, it was a peaceful stay!"
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

9.8 out of 10, Exceptional, (35)
"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."
The price is AU$445
includes taxes & fees
17 Oct - 18 Oct
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

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

9.8 out of 10, Exceptional, (29)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Blue Loon Camp on Pleasant Pond in Litchfield

9.6 out of 10, Exceptional, (8)
"This comfy cabin can sleep 6 people no problem! With a close quarters experience made staying more the fun! EasyAccess to kayaks and canoes was awesome. Had a couple Beavers going back n forth in front of the cabin as well! Bailey the Neighbor dog stopped by to say hi in the yard along with Chancellor and Lous minutes prior. Thanks again for your accommodations. We would love to visit again in the future! "
Blue Loon Camp on Pleasant Pond in Litchfield

3 Bedroom Happy Cottage 15

10.0 out of 10, Exceptional, (1)
"This house is highly recommended; we had a fantastic stay! New, nice, and clean. Check-in and check-out were a breeze; and communication with the owner was fantastic."
3 Bedroom Happy Cottage 15

Just steps to the water with beautiful sunsets!

10.0 out of 10, Exceptional, (37)
"Great location. Quiet relaxed venue with all you would need for a relaxing vacation"
Just steps to the water with beautiful sunsets!

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (19)
"Very nice weekend and great host- very responsive!"
Cozy Long Pond Cottage: private mooring & shared dock

Come Spring Farm Glamping Dome 2

10.0 out of 10, Exceptional, (1)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
The price is AU$388
includes taxes & fees
13 Oct - 14 Oct
Come Spring Farm Glamping Dome 2

Waterfront 2br/2ba cottage

9.8 out of 10, Exceptional, (15)
"This was a great place to stay, cental to places we wanted to see. Has water acess and lots of toy/boat options. Saw some loons, fireflies and the friendly free range chickens that would wonder around."
The price is AU$494
includes taxes & fees
5 Oct - 6 Oct
Waterfront 2br/2ba cottage

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (6)
"Great stay. Would stay here again if in the area."
The price is AU$355
includes taxes & fees
6 Oct - 7 Oct
Sister A-Frame in Woods B

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

8.0 out of 10, Very good, (8)
"Fit our needs perfectly!"
Peaceful home with forest views & great yard - minutes to town

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

9.0 out of 10, Wonderful, (7)
"Beautiful location and a unique stay."
The price is AU$340
includes taxes & fees
16 Oct - 17 Oct
Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Spacious 1 Bedroom Close to Everything 4

9.8 out of 10, Exceptional, (21)
"This unit fit all of our needs regarding location, cleanliness, and amenities. I would 100% recommend this property to my friends and family and will revisit this if I'm in town in the future!"
Spacious 1 Bedroom Close to Everything 4

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

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Large New Lakeside Cottage Central Air

8.4 out of 10, Very good, (36)
"We loved the cabin, even in rainy weather. "
Large New Lakeside Cottage Central Air

Kayakers’ Cabin- “Maine Cabin Masters” remodel.

10.0 out of 10, Exceptional, (50)
"My 3 girlfriends and I stayed at Luke and Laura’s cozy lake side cabin in late June and I highly recommend it to anyone visiting the Newcastle area. The location was perfect, just under ten minutes from the main st area, with a ton of options to eat and shop! I highly recommend sunny side for breakfast and the shuck shack for lunch or dinner. "
Kayakers’ Cabin- “Maine Cabin Masters” remodel.

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

10.0 out of 10, Exceptional, (15)
"Beautiful property, had everything that was needed. Would definitely book again!"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

9.8 out of 10, Exceptional, (27)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
The price is AU$344
includes taxes & fees
30 Oct - 31 Oct
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Lakefront Cabin

10.0 out of 10, Exceptional, (27)
"Enjoyed an awesome stay on the lake!! House was super and Kennith was a great host!"
Lakefront 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

Find out more about Windsor

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

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

Windsor holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$340 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select 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 holiday rentals that Windsor has to offer?

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

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 Kennebec River Rail Trail. In the wider area, you’ll find Old Fort Western and Capitol Park.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.