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Top Holiday Rentals in Windsor

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

9.6 out of 10, Exceptional, (53)
"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

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (111)
"Perfect place to hang by the water and sit in the large porch all day. Wish we had more time there! "
A Charming Waterfront Cottage with Touches of Elegance

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

8.6 out of 10, Excellent, (4)
"Fit our needs perfectly!"
Peaceful home with forest views & great yard - minutes to town

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 !

“STEP BACK IN TIME” 1880’ charmer.<br>Riverside Cottage<br>

9.6 out of 10, Exceptional, (40)
"The house was lovely, beautifully situated and everything was clean and comfortable !"
“STEP BACK IN TIME” 1880’ charmer.<br>Riverside Cottage<br>

Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream

10.0 out of 10, Exceptional, (65)
"The cottage was perfect for a post Christmas relaxing week of downtime."
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream

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

10.0 out of 10, Exceptional, (38)
"Very clean and comfortable."
Driftwood Cottage with Cottages of Maine, Lake Great Pond, Dog Friendly, Kayaks

Kayakers’ Cabin- “Maine Cabin Masters” remodel.

10.0 out of 10, Exceptional, (42)
"This rental was exactly as presented, with great waterfront views of the lake, and easy access to the town of Damariscotta."
Kayakers’ Cabin- “Maine Cabin Masters” remodel.

Dome 1 - Luxury Dome at Come Spring Farm

9.6 out of 10, Exceptional, (9)
"We had a great experience with our stay Everything was nice the owner was very helpful and friendly "
The price is £229
includes taxes & fees
3 Jul - 4 Jul
Dome 1 - Luxury Dome at Come Spring Farm

Get in touch with nature.

10.0 out of 10, Exceptional, (22)
"Nice location, beautiful tent, quiet place among the forest. Great for a retreat"
The price is £114
includes taxes & fees
7 Jul - 8 Jul
Get in touch with nature.

The Modern Maine Retreat

9.0 out of 10, Wonderful, (4)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

7.0 out of 10, Good, (2)
"Beautiful location and a unique stay."
The price is £189
includes taxes & fees
3 Jul - 4 Jul
Dome 3 at Come Spring Farm Glamping - Alpaca Farm

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

9.8 out of 10, Exceptional, (28)
"This place was perfect for our 3-night stay. Inside, it hits the sweet spot between well-equipped but uncluttered. The bird-watching overlooking the water was fantastic - from huge bald eagles to petite hummingbirds. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

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

10.0 out of 10, Exceptional, (6)
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Come Spring Farm Glamping Dome 2

The price is £211
includes taxes & fees
10 Jul - 11 Jul
Come Spring Farm Glamping Dome 2

Lakefront Escape w/ Dock, Fire Pit & Views

Lakefront Escape w/ Dock, Fire Pit & Views

Private Dock & Deck: Tranquil Dam Pond Cottage!

10.0 out of 10, Exceptional, (3)
"Restful retreat with everything you need. From the sound of the loons, the comfortable accommodations, accessibility to so many great spots, and wonderful hosts you can't beat it. Can't wait to come back. "
Private Dock & Deck: Tranquil Dam Pond Cottage!

Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

9.2 out of 10, Wonderful, (12)
"Such a nice little spot to relax on the lake."
Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

Large New Lakeside Cottage Central Air

8.2 out of 10, Very good, (32)
"Classic Maine lake property - great as a home base for lake activities. House held our 8 people nicely and was as advertised with a responsive host."
Large New Lakeside Cottage Central Air

Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok

9.2 out of 10, Wonderful, (20)
"We are repeat customers. A quiet, clean, scenic, winter getaway. A great place to unplug and recharge. We will continue to be repeat customers! "
Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok
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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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?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a patio and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Samantha Smith, or get outside and enjoy nature at Kennebec River Rail Trail. In the wider area, you’ll find Kennebec Arsenal and Old Fort Western.

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.