Windsor Holiday Rentals

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Holiday Rentals in Windsor

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"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 !

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (111)
"My husband and our 1 year old daughter had a wonderful stay. The home is close to everything and has everything you may need. Would love to stay again. "
A Charming Waterfront Cottage with Touches of Elegance

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.6 out of 10, Excellent, (11)
"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 AU$498
includes taxes & fees
17 Aug - 18 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee

Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

9.0 out of 10, Wonderful, (2)
"Cozy cottage by the lake. Great scenery and wildlife. Great communication with host. "
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

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

2.0 star property
9.0 out of 10, Wonderful, (102)
"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

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

10.0 out of 10, Exceptional, (53)
"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, (27)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is AU$554
includes taxes & fees
17 Aug - 18 Aug
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

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

9.4 out of 10, Exceptional, (56)
"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

Peaceful Lakefront Maine Cabin w/ Sunset Views

Peaceful Lakefront Maine Cabin w/ Sunset Views

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

8.8 out of 10, Excellent, (5)
"Your home is beautiful!! Love all the windows, very comfortable!!"
Peaceful home with forest views & great yard - minutes to town

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

10.0 out of 10, Exceptional, (68)
"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

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

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

Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

9.8 out of 10, Exceptional, (27)
"This was an amazing experience and the vision that the owners have is amazing I highly recommend this place"
The price is AU$349
includes taxes & fees
5 Aug - 6 Aug
Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

9.0 out of 10, Wonderful, (21)
"Great view, clean, central a/c, even the ppl using powerboats (4th of July!) were respectful. Exactly the getaway I needed!"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Large New Lakeside Cottage Central Air

8.2 out of 10, Very good, (33)
"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

Spacious 1 Bedroom Close to Everything 4

10.0 out of 10, Exceptional, (17)
"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

Lighthouse Lane

10.0 out of 10, Exceptional, (58)
"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 AU$921
includes taxes & fees
2 Sept - 3 Sept
Lighthouse Lane

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

9.8 out of 10, Exceptional, (31)
"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

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (3)
"Great stay. Would stay here again if in the area."
The price is AU$357
includes taxes & fees
7 Aug - 8 Aug
Sister A-Frame in Woods B

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.6 out of 10, Exceptional, (5)
"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!
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

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.