Windsor Holiday Rentals

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Holiday Rentals in Windsor

Classy AF Home Steps from Colby and Trails

Oakland
10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails

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

Sidney
9.8 out of 10, Exceptional, (35)
"Very nice hot tub, quite and beautiful area! Air quality amazing and AC works fantasticly!"
United States
Nathan
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Private and Calming Waterfront to the Rescue!

Augusta
9.8 out of 10, Exceptional, (86)
"Absolutely amazing property, everything we were looking for and an amazing host too! Highly recommend! "
United States
samantha c.
Private and Calming Waterfront to the Rescue!

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.8 out of 10, Excellent, (17)
"Check in was a breeze. Right on the lake. House was just the right size for me and my 3 adult sons. Was lovely to paddle, canoe or swim just walking down the porch stairs"
United States
Heather A.
The price is AU$497
includes taxes & fees
19 Nov - 20 Nov
Cozy Cottage on water's edge of Lake Cobbosseecontee

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 !

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"My family and I attended a concert at the Bowl in the Pines and wanted to make a weekend out of it and found this perfect little cabin right on the lake! Kids absolutely loved swimming, fishing and canoeing! Great spot for family bonding! Thank you! "
United States
Laura L.
Lakefront Cabin

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.
The price is AU$445
includes taxes & fees
19 Nov - 20 Nov
Waterfront 2br/2ba cottage

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

Wiscasset
7.8 out of 10, Good, (9)
"Fit our needs perfectly!"
United States
Aimee K.
Peaceful home with forest views & great yard - minutes to town

Cozy House in the heart of Waterville Maine.

Waterville
9.6 out of 10, Exceptional, (48)
"Loved the cozy home! We would stay there again in a heartbeat. The only thing that we would have been nice is if there was a tv in the main bedroom, but that’s just a personal preference. "
United States
Michelle
Cozy House in the heart of Waterville Maine.

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

Oakland
9.4 out of 10, Exceptional, (66)
"Beautiful lake, beautiful property, nice hiking"
United States
Darcy M.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Get in touch with nature.

Richmond
10.0 out of 10, Exceptional, (35)
"Very peaceful and clean "
United States
Lori m.
Get in touch with nature.

Ice Fishing, Dog Friendly, Lake Great Pond

Belgrade
10.0 out of 10, Exceptional, (48)
"The house was great, and the owners were very communicative and responsive. Would definitely recommend and stay again!"
United States
Jonathon R.
The price is AU$475
includes taxes & fees
24 Nov - 25 Nov
Ice Fishing, Dog Friendly, Lake Great Pond

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AU$356
includes taxes & fees
19 Nov - 20 Nov
Sister A-Frame in Woods B

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

Mount Vernon
10.0 out of 10, Exceptional, (20)
"Beautiful property, had everything that was needed. Would definitely book again!"
United States
Rachel G.
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

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

Mount Vernon
10.0 out of 10, Exceptional, (2)
"This house was absolutely stunning! Had absolutely everything that you needed the house offered everything that one would need and plenty of space for everybody! The game room was so fun! The hot tub was a great bonus! Everyone had an amazing time while staying."
United States
Rachael L.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Large New Lakeside Cottage Central Air

Belgrade
8.4 out of 10, Very good, (37)
"Totally enjoyed our trip. This is the 2nd time we've stayed here. John is a great host. "
United States
Irene D.
Large New Lakeside Cottage Central Air

Dome 1 - Luxury Dome at Come Spring Farm

Union
9.6 out of 10, Exceptional, (17)
"Amazing adventure. Would highly recommend!"
United States
Julie H.
Dome 1 - Luxury Dome at Come Spring Farm

Cozy Long Pond Cottage: private mooring & shared dock

Rome
9.8 out of 10, Exceptional, (20)
"We had a great time kayaking on the lake and enjoying the beach. The house had plenty of room to get together with family for dinners. The house is well equipped and very comfortable."
United States
Jim U.
Cozy Long Pond Cottage: private mooring & shared dock

Sunfish Cove is the perfect year round getaway.

Monmouth
10.0 out of 10, Exceptional, (51)
"Awesome property for an extended family stay"
United States
shannon p.
Sunfish Cove is the perfect year round getaway.

Spacious 1 Bedroom Cottage Close to Everything 5

Edgecomb
10.0 out of 10, Exceptional, (10)
"This place was an awesome weekend staycation soot"
United States
William B.
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

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$356 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?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: This holiday home rental outside of Windsor is located in a rural location, and has 1 hot tub, a BBQ 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 that 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 wider area, you’ll find Old Fort Western and Maine State House.

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.