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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Windsor holiday rentals

Cottage (2 Bedrooms) | Interior

Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
The price is 3.786.048 ₫
10.612.503 ₫ total
includes taxes & fees
16 Aug - 17 Aug
Rustic Retreat Across From Lake; Family Friendly!
House (3 Bedrooms) | Front of property

Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
The price is 4.758.852 ₫
12.899.907 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Near Lakes, Bay & Trails! Historic Waldoboro Gem
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

Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

8/10 Good
"Very good location and great sunsets out the balconies or just drive down to the water for beautiful shots. Room was clean and comfortable, if a bit basic. The loveseat was extremely uncomfortable. Breakfast was basic but staff were friendly."
CHARLENE 1-night trip
Posted 10 hours ago
Cod Cove Inn, BW Signature Collection

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 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 Threemile Pond. 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.