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Top Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.8 out of 10, Excellent, (12)
"Great little getaway, sitting right by the water. We loved our time there. Alarice is a great hot and responded quickly to any needs or questions."
The price is £241
includes taxes & fees
27 Aug - 28 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee

Nature lovers Paradise your own island

9.8 out of 10, Exceptional, (67)
"Amazing property! "
Nature lovers Paradise your own island

Peaceful.... Lakefront Cottage... Kayakers Paradise....

10.0 out of 10, Exceptional, (56)
"Beautiful, peaceful location. Great fishing. Comfortable, immaculate cabin."
Peaceful.... Lakefront Cottage... Kayakers Paradise....

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (30)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is £256
includes taxes & fees
8 Sept - 9 Sept
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (144)
"Best location on lake. House was warm and recently updated. Fun time "
Updated lake cottage right on Damariscotta Lake.

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"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 !

Lighthouse Lane

10.0 out of 10, Exceptional, (62)
"Check in and check out was super easy. Photos are super accurate and the property is beautiful. Thank you for sharing your beautiful with us!"
The price is £406
includes taxes & fees
2 Sept - 3 Sept
Lighthouse Lane

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

9.4 out of 10, Exceptional, (60)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Charming cabin in the birches right on the atv trail!

2.0 star property
9.0 out of 10, Wonderful, (6)
"I felt very comfortable. It's a very nice cabin, it has all the amenities, and it's perfect for sharing as a couple or as a family. I had a great time."
The price is £151
includes taxes & fees
27 Aug - 28 Aug
Charming cabin in the birches right on the atv trail!

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.0 out of 10, Wonderful, (6)
"Great spot right on the lake, True to what was listed. The beds weren’t very comfortable but otherwise everything was great."
Private Dock on Messalonskee Lake: Cozy Cottage!

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (39)
"Very comfortable and clean VRBO!The hosts were very kind and easy to work with!!Great location for getting into Colby Highly recommend this location for people visiting in the area"
The price is £187
includes taxes & fees
31 Aug - 1 Sept
Central Maine Apartment offering 4 Seasons of Fun.

Cabin China Lake

9.6 out of 10, Exceptional, (13)
"Second time there and is always nice. "
Cabin China Lake

Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK

2.0 star property
9.0 out of 10, Wonderful, (103)
"The place was very clean. Right on the water. Spectacular views. Sunrise in the morning. A great experience. A lovely get away. Want to go back again"
Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK

New Waterfront Lake House - completed 2021

10.0 out of 10, Exceptional, (27)
"We love this place, it's the perfect Lake House and we intend on staying every year!"
New Waterfront Lake House - completed 2021

Blue Loon Camp on Pleasant Pond in Litchfield

8.8 out of 10, Excellent, (3)
"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

Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

10.0 out of 10, Exceptional, (44)
"Very clean and comfortable."
The price is £277
includes taxes & fees
28 Aug - 29 Aug
Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

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

10.0 out of 10, Exceptional, (11)
"Nice time"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

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

7.8 out of 10, Good, (6)
"Your home is beautiful!! Love all the windows, very comfortable!!"
Peaceful home with forest views & great yard - minutes to town

Spacious 1 Bedroom Close to Everything 4

9.8 out of 10, Exceptional, (19)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Spacious 1 Bedroom Close to Everything 4

Beachfront Cottage Nestled in a Cove

10.0 out of 10, Exceptional, (2)
"Enjoyed our stay in the cottage. Loved the view of the lake. Nice to get away from it all and enjoy a relaxing few days on the water."
Beachfront Cottage Nestled in a Cove
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, apart-hotels, 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 favorite 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 depends 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 £151 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 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?

Cozy Cottage on water's edge of Lake Cobbosseecontee: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.