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Featured Cottages in New Windsor

Mountain View escape

Mountain View escape

New Paltz
Located in New Paltz, this cottage is within a 10-minute drive of Jenkinstown Day Spa and Loren Campbell Memorial Field.
Mountain View escape
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
The price is AU$425 per night from 1 Apr to 2 Apr
AU$425
includes taxes & fees
1 Apr - 2 Apr
When you stay at this cottage in Fort Montgomery, you'll be on a river, within a 15-minute drive of Bear Mountain State Park and United States Military ...
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks

Charming Cottage in the Heart of the Shawangunks

Wallkill
The price is AU$851 per night from 13 Apr to 14 Apr
AU$851
includes taxes & fees
13 Apr - 14 Apr
Located in Wallkill, this cottage is on a river, a 1-minute drive from Minnewaska State Park and 10 minutes from Whitecliff Vineyard.
Charming Cottage in the Heart of the Shawangunks
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Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!

Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!

Fishkill
With a stay at this cottage in Fishkill, you'll be within a 5-minute drive of Hudson Highlands State Park and Van Wyck Homestead Museum.
Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!
Be in Nature at this Gorgeous Riverfront Cabin

Be in Nature at this Gorgeous Riverfront Cabin

Poughkeepsie
When you stay at this cottage in Poughkeepsie, you'll be on a river, within a 15-minute drive of Vassar College and Marist College.
Be in Nature at this Gorgeous Riverfront Cabin
A romantic cottage and artist's retreat looking down over an enchanted lake

A romantic cottage and artist's retreat looking down over an enchanted lake

Greenwood Lake
When you stay at this cottage in Greenwood Lake, you'll be on a lake, within a 5-minute drive of Greenwood Lake and Lion's Field Park.
A romantic cottage and artist's retreat looking down over an enchanted lake
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

Warwick
Located in Warwick, this cottage is in a rural location, within a 5-minute drive of Mount Peter Hawk Watch Trailway and Continental Road Trailhead.
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Historic 1800's Cornwall-On-Hudson Cottage!

Historic 1800's Cornwall-On-Hudson Cottage!

Cornwall-On-Hudson
With a stay at this cottage in Cornwall, you'll be within a 10-minute drive of United States Military Academy and New York Military Academy.
Historic 1800's Cornwall-On-Hudson Cottage!
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Kerhonkson
The price is AU$304 per night from 29 Apr to 30 Apr
AU$304
includes taxes & fees
29 Apr - 30 Apr
Located in Kerhonkson, this cottage is in the mountains, within a 5-minute drive of Minnewaska State Park and Lake Minnewaska Beach.
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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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.

New Windsor Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in New Windsor will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to New Windsor definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in New Windsor, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

New Windsor Cottages essential information

Accommodation
90 Cottages
Lowest Price
AU$176
Highest Price
AU$851
Popular accommodation
Mountain View escape, Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands, Charming Cottage in the Heart of the Shawangunks, Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!, Be in Nature at this Gorgeous Riverfront Cabin, A romantic cottage and artist's retreat looking down over an enchanted lake, Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick, Historic 1800's Cornwall-On-Hudson Cottage!, Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Top trending hotels in New Windsor

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 6 Apr to 7 Apr
AU$196
includes taxes & fees
6 Apr - 7 Apr
Located in New Windsor, Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point is within a 5-minute drive of Hamilton Fish Bridge and National Purple Heart ...
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is AU$245 per night from 17 Apr to 18 Apr
AU$245
includes taxes & fees
17 Apr - 18 Apr
With a stay at Homewood Suites Stewart Airport in New Windsor, you'll be within a 5-minute drive of National Purple Heart Hall of Honor and Hamilton Fish ...
Homewood Suites Stewart Airport
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is AU$188 per night from 1 Apr to 2 Apr
AU$188
includes taxes & fees
1 Apr - 2 Apr
When you stay at Overlook Lodge at Bear Mountain in Bear Mountain, you'll be in a state park, a 1-minute drive from Bear Mountain State Park and 7 minutes from ...
Overlook Lodge at Bear Mountain
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Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 17 Apr to 18 Apr
AU$176
includes taxes & fees
17 Apr - 18 Apr
With a stay at Sleep Inn & Suites Middletown - Goshen, you'll be centrally located in Middletown, within a 15-minute drive of LEGOLAND® New York and Paramount ...
Sleep Inn & Suites Middletown - Goshen
Don't see what you're looking for?
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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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^Subject to availability and chosen travel dates.