New Windsor Holiday Rentals

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Holiday Rentals in New Windsor

Relax by the Rock River, book our cozy 1-bedroom cabin

9.8 out of 10, Exceptional, (17)
"Wonderful fully finished interior, great for a weekend with friends. Hosts are gracious and prompt, and overall we had a lovely time. We always stay here during the fall, it's fastbecomingna tradition!"
Relax by the Rock River, book our cozy 1-bedroom cabin

Rustic and Secluded 1 Bedroom Cabin Retreat. Located on Private Stocked Pond.

10.0 out of 10, Exceptional, (26)
"Had a great experience taking our dog for her first overnight in a strange place. Quiet, peaceful place for relaxing and reconnecting. Cabin had all the amenities needed and hosts were awesome to work with. "
Rustic and Secluded 1 Bedroom Cabin Retreat. Located on Private Stocked Pond.

Home on the Green River!

10.0 out of 10, Exceptional, (31)
"The property was great. Clean and comfortable. The host were great with all questions i had very helpful. Thank you so much i would stay again."
Home on the Green River!

*Rare River Cottage w/ fantastic views*

9.4 out of 10, Exceptional, (25)
"We had a very nice, relaxing stay at this property. It's a nice layout with a large deck and a small playhouse detached from the primary home. It would be perfect for kids. It does not have a whirlpool which was no problem for us. There was a pontoon boat at the end of a very short peer which would have made it difficult to get the canoe in the water so we elected not to try it as it was a very rocky shore and we're kind of old.. The sunsets were beautiful as advertised. There was a pretty...
The price is AU$358
includes taxes & fees
11 Dec - 12 Dec
*Rare River Cottage w/ fantastic views*

Riverside Treehouse

10.0 out of 10, Exceptional, (11)
"We had a nice relaxing weekend. The house is very clean and in a quite neighborhood. It is close to restaurants, a mall, movie theater and grocerie store (walmart)."
Riverside Treehouse

Rustic dog-friendly cabin with fireplace, open layout, grill, W/D, & firepit

10.0 out of 10, Exceptional, (7)
"Great property that feels secluded but was just on the edge of town."
Rustic dog-friendly cabin with fireplace, open layout, grill, W/D, & firepit

Riverside Cottage

9.8 out of 10, Exceptional, (39)
"The house was great and it was fun to be right on the water! The furniture was all very comfortable too. There wasn’t enough silverware , only like 3 spoons and 3 forks. Also the outdoor furniture was all covered in spider webs. Overall a great place to stay!"
Riverside Cottage

Rock Island Home w/ Private Yard & Fire Pit Table!

10.0 out of 10, Exceptional, (2)
"This beautiful and roomy home was a great size for our adult family of five. It has a lovely patio with plenty of comfortable seating options. Large private back yard. The home was very clean. We would definitely stay at this home when we are in the area again."
Rock Island Home w/ Private Yard & Fire Pit Table!

Rock Island Home w/ Private Yard & Fire Pit Table!

3.0 star property
Rock Island Home w/ Private Yard & Fire Pit Table!
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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Other types of properties in New Windsor you may be interested in

Baymont by Wyndham Galesburg

2.5 star property
8.2 out of 10, Very good, (1064)
"We love the staff at this hotel. We stay here every time we come to visit this area "
The price is AU$138
includes taxes & fees
1 Dec - 2 Dec
Baymont by Wyndham Galesburg

Best Western Airport Inn

2.5 star property
8.4 out of 10, Very good, (993)
"Helpful staff, clean & quiet"
The price is AU$104
includes taxes & fees
2 Dec - 3 Dec
Best Western Airport Inn

Country Inn & Suites by Radisson, Moline Airport, IL

2.5 star property
8.2 out of 10, Very good, (1014)
"it was close to airport to take our son back to fly home to the Philippines and price was not bad either for one night "
The price is AU$118
includes taxes & fees
12 Dec - 13 Dec
Country Inn & Suites by Radisson, Moline Airport, IL
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in New Windsor?

Yes, there are holiday rentals close to the most popular sights in New Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that New Windsor has to offer?

Home on the Green River!: This holiday home rental outside of New Windsor is located on a river, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchenette with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in New Windsor?

While exploring the area, visit family-friendly sights like Lakeside Water Park, or get outside and enjoy nature at Lake Storey. In the wider area, you’ll find Carl Sandburg College and Creekside Vineyards.

What are holiday rentals like in New Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Windsor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.