Title: New Windsor Vacation Rentals from $269: Search Short-Term Rentals | Expedia.com

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![](https://images.trvl-media.com/place/6148010/b4469cf7-6c52-4383-a18b-1573522aca84.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Wanderlustfemale

![](https://images.trvl-media.com/place/6148010/b4469cf7-6c52-4383-a18b-1573522aca84.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=10021&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for New Windsor vacation rentals

![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/e25829b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/8d663c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1616e5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116370000/116362400/116362325/1ae526bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Cabin with Pool & Fire Pit

[](https://www.expedia.com/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information)

Montgomery

10/10

Exceptional

(3 reviews)

"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah A.

$185 nightly

$209 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Montgomery-Hotels-Cozy-Cabin-Gateway-I-15-Acres-W-Pool-Firepit.h116362325.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/315d7b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/2dce554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/cdecc2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83440000/83439600/83439540/d9bc7fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

[](https://www.expedia.com/Kerhonkson-Hotels-Dream-House-In-The-Gunks.h83439540.Hotel-Information)

Kerhonkson

10/10

Exceptional

(34 reviews)

"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julia K.

$175 nightly

$177 total

Apr 15 - Apr 16

Total with taxes and fees

[](https://www.expedia.com/Kerhonkson-Hotels-Dream-House-In-The-Gunks.h83439540.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y2-21ff539b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-8188dd85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y0-cfce0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-d877abc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the Heart of the Hudson Valley, Cabin 1

[](https://www.expedia.com/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information)

Newburgh

10/10

Exceptional

(32 reviews)

"Great overnight spot, especially with a dog."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed C.

$236 nightly

$279 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

[](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

Fort Montgomery

9.8/10

Exceptional

(134 reviews)

"Amazing place Thanks for the stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Julien C.

$271 nightly

$271 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/ef9b23f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/c86208ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/02671128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111190000/111183400/111183358/b07ff9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

[](https://www.expedia.com/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information)

Fishkill

9.4/10

Exceptional

(62 reviews)

"For us it was in a great location, had a reasonable price and room for everyone."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gertrude (Gert) P.

$280 nightly

$323 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Fishkill-Hotels-Large-Relaxing-Family-Retreat-In-The-Hudson-Valley-With-Theatre-And-Gazebo.h111183358.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/4c32f4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w1024h677x0y3-47c781b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w1024h680x0y3-a7b1dcac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w906h683x59y0-429ea470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in the heart of the Hudson Valley, Cabin 4

[](https://www.expedia.com/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899463.Hotel-Information)

Newburgh

9.0/10

Wonderful

(26 reviews)

"We LOVE this place and have stayed here twice."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

jennifer w.

$169 nightly

$200 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899463.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/10d69ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/fd01a6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/0c3ccbf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/cb371140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dream getaway apartment in the foot of Gunks Ridge

[](https://www.expedia.com/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information)

Wallkill

9.6/10

Exceptional

(24 reviews)

"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary S.

$169 nightly

$171 total

Apr 23 - Apr 24

Total with taxes and fees

[](https://www.expedia.com/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/1fe9eea3_edited_074f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/5eb61507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/92eb238a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116760000/116758500/116758499/92496678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Cozy private suite in the heart of beautiful Gardiner.

[](https://www.expedia.com/New-Paltz-Hotels-Cozy-Private-Suite-In-The-Heart-Of-Beautiful-Gardiner.h116758499.Hotel-Information)

New Paltz

10/10

Exceptional

(7 reviews)

"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chanah B.

$218 nightly

$244 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/New-Paltz-Hotels-Cozy-Private-Suite-In-The-Heart-Of-Beautiful-Gardiner.h116758499.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/38809636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/07a03d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/416c2b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101950000/101941800/101941777/cfa82cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike. 

[](https://www.expedia.com/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information)

Carmel Hamlet

9.8/10

Exceptional

(13 reviews)

"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hannah P.

$364 nightly

$394 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Carmel-Hotels-Lux-Bungalow-On-Gorgeous-Lake-Relax-Explore-Nearby-Towns-Ski-Kayak-Hike.h101941777.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/13d8fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/0f1e7af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/99922af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/7dc21331_edited_faa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

[](https://www.expedia.com/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

Putnam Valley

9.8/10

Exceptional

(23 reviews)

"Great, clean house, nice accommodating host. Would stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Heather T.

$468 nightly

$516 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/6a09d677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/e5c54a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/3207c5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105180000/105177900/105177891/f77cbaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely 3BR Home with parking-Walk to WP Gate!

[](https://www.expedia.com/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

Highland Falls

10/10

Exceptional

(7 reviews)

"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Briana T.

$287 nightly

$324 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Highland-Falls-Hotels-Lovely-3BR-Home-With-Parking-Walk-To-WP-Gate.h105177891.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/32d0bc6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/449fc3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/e5a3641b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102150000/102145900/102145832/d9fd7f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Contemporary Cozy Cottage

[](https://www.expedia.com/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

Lake Peekskill

9.8/10

Exceptional

(32 reviews)

"Very clean comfortable quiet place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mauro C.

$370 nightly

$423 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Lake-Peekskill-Hotels-Contemporary-Cozy-Cottage.h102145832.Hotel-Information)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/dd930402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/1cd6d553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/2c8ccdec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717464/328adef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

[](https://www.expedia.com/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.Hotel-Information)

Highland Falls

9.8/10

Exceptional

(18 reviews)

"Great Unit."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rudy R.

$302 nightly

$307 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Highland-Falls-Hotels-Quiet-Apt-With-Coffee-Bar.h94717464.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69540000/69532700/69532688/655f4735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69540000/69532700/69532688/6b59c530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69540000/69532700/69532688/d7e6e4ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/70000000/69540000/69532700/69532688/59867d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax! 

[](https://www.expedia.com/Wallkill-Hotels-Waterfront-Modern-1bd-10-Min-To-Mtns-Wineries.h69532688.Hotel-Information)

Wallkill

10/10

Exceptional

(79 reviews)

"great location and nice host"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

christopher s.

$240 nightly

$269 total

Apr 20 - Apr 21

Total with taxes and fees

[](https://www.expedia.com/Wallkill-Hotels-Waterfront-Modern-1bd-10-Min-To-Mtns-Wineries.h69532688.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/541d91ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/537494b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/d2d9d4e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/78000000/77290000/77280600/77280503/5a612bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country House w/Hot Tub, Deck, Grill & Fire Pit

[](https://www.expedia.com/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information)

Goshen

10/10

Exceptional

(61 reviews)

"Very good host "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Binyomin

$478 nightly

$499 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Goshen-Hotels-Renovated-House-WHot-Tub.h77280503.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/a27e5755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/5e31b747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/41dec043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/46000000/45750000/45742900/45742802/03710a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy country efficiency in the Hudson Valley

[](https://www.expedia.com/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.Hotel-Information)

Newburgh

9.8/10

Exceptional

(68 reviews)

"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lou F.

$269 nightly

$318 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Newburgh-Hotels-Cozy-Country-Efficiency-In-The-Hudson-Valley.h45742802.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/424d87c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/e73b5292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/9832ea44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113530000/113522300/113522235/92f8429f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House on the Babbling Brook- Quiet 2BR + King Bed!

[](https://www.expedia.com/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

Highland Falls

10/10

Exceptional

(8 reviews)

"Good stay, awesome place"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott G.

$371 nightly

$393 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Highland-Falls-Hotels-House-On-The-Babbling-Brook-Quiet-2BR-King-Bed.h113522235.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/be15b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/116022ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/8cbcd139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114380000/114378800/114378708/ab2c7ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fabulous 3bdrm Home w/parking!

[](https://www.expedia.com/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

Highland Falls

9.2/10

Wonderful

(5 reviews)

"Clean home, conveniently located to West Point. Very comfortable beds. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle B.

$280 nightly

$308 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Highland-Falls-Hotels-Fabulous-3bdrm-Home-Wparking.h114378708.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/bf85ab49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/9714c3f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/96050ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107970000/107964300/107964203/75814d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

[](https://www.expedia.com/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information)

Gardiner

10/10

Exceptional

(11 reviews)

"Great weekend getaway to reconnect with old friends!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa D.

$251 nightly

$254 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Gardiner-Hotels-Modern-Zen-Chalet-At-The-Foot-Of-Gunks-W-Mt-View.h107964203.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/125000000/124060000/124052800/124052744/2f040710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124060000/124052800/124052744/35068c8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124060000/124052800/124052744/d44795b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124060000/124052800/124052744/44968177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury House Near West Point

[](https://www.expedia.com/Highland-Falls-Hotels-Luxury-House-Near-West-Point.h124052744.Hotel-Information)

Highland Falls

$310 nightly

$325 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Highland-Falls-Hotels-Luxury-House-Near-West-Point.h124052744.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-17&endDate=2026-04-18&regionId=10021&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CABIN)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VACATION_HOME)

Villas

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VILLA)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CONDO)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=New+Windsor%2C+New+York%2C+United+States+of+America&regionId=10021&latLong=41.476761%2C-74.02375&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CHALET)

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## Top New Windsor Hotel Reviews

![Hyatt Place Poughkeepsie / Hudson Valley](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg)

### Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"Reception was great! Quick check-in and checkout. Thank you!"

[](https://expedia.com/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information)

![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/875b6b8c_y.jpg)

### DoubleTree by Hilton Poughkeepsie Convention Center

2/10 Terrible

"When I returned to my room, it was 80 degrees even though the thermostat was set to 68\. I went to the front desk and they sent maintenance. Maintenance told me there wasn't anything they could do because the air conditioning isn't working. He even showed me another room to show that it would be just as hot. Nobody should have to be stuck in a room this hot, especially when they're paying for the room and a ridiculous $600 dollar deposit on top of it. It's not even that the a/c doesn't work; they just don't have it on and refuse to turn it on. The staff didn’t offer any remedy, or do anything to help. They just simply handled it with a “There’s nothing we can do.” I stay here whenever I visit my brother, but from now on, I’ll be staying somewhere else. "

[](https://expedia.com/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information)

![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg)

### Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"We had a great stay! Our room was clean, and the hotel was conveniently located just a 15-minute drive from LEGOLAND. The breakfast was also pretty good, which was a nice bonus. We would definitely stay here again!"

[](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information)

![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/1ee75d40_y.jpg)

### Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Beautiful hotel with a vibrant lobby/restaurant/bar area. Rooms are spacious and well appointed. Hotel is very clean and staff is friendly. Can’t wait to return there! "

[](https://expedia.com/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information)

![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg)

### Hampton Inn Harriman Woodbury

8/10 Good

"Great"

[](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information)

![Hampton Inn by Hilton New Paltz](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b_y.jpg)

### Hampton Inn by Hilton New Paltz

10/10 Excellent

"There was a decent assortment of breakfast items including 3 hot breakfast items, bagels, oatmeal, fresh fruit etc."

[](https://expedia.com/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.Hotel-Information)

![Holiday Inn Express Fishkill-Mid Hudson Valley by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/5b94363e_y.jpg)

### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

10/10 Excellent

"The staff was very friendly and courteous. The room was Great! They provide "Dove" soaps and lotions. The bathroom floor was super slippery after you shower. The breakfast was nice. There was a nice variety. The juice machine wasnt working during our stay, but they had bottles of yummy chocolate milk. I was hoping for bacon as shown in one of the photos, its my favorite, but there was sausage, which was good too. The pool was nice. The jets in the hot tub were barely working. Overall, I'd deff stay there again."

[](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information)

![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg)

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

8/10 Good

"Parking was great. Rooms were clean. "

[](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information)

![Wildflower Farms, Auberge Collection](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/2028d4aa_y.jpg)

### Wildflower Farms, Auberge Collection

10/10 Excellent

"Everything was superb. Beautiful facilities. Impeccable service. Flawless attention to detail. Terrific style. Delicious food. Wonderful activities. Absolutely divine! One of the best vacations I have ever had, and one of the most delightful properties I have ever visited."

[](https://expedia.com/Gardiner-Hotels-Wildflower-Farms.h79873064.Hotel-Information)

## Find out more about New Windsor

**Everything you need to know about New Windsor vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**New Windsor vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in New Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $269 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on New Windsor rentals**

At Expedia, we put the best New Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
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- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in New Windsor ](https://expedia.com/New-Windsor-Private-Vacation-Homes.d10021-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in New Windsor ](https://expedia.com/New-Windsor-Apartments.d10021-aaApartments.Travel-Guide-Accommodation)
- [Cottages in New Windsor ](https://expedia.com/New-Windsor-Cottages.d10021-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in New Windsor ](https://expedia.com/New-Windsor-Cabins.d10021-aaCabins.Travel-Guide-Accommodation)
- [Villas in New Windsor ](https://expedia.com/New-Windsor-Villas.d10021-aaVillas.Travel-Guide-Accommodation)
- [Motels in New Windsor ](https://expedia.com/New-Windsor-Motels.d10021-aaMotels.Travel-Guide-Accommodation)
- [B&B in New Windsor ](https://expedia.com/New-Windsor-Bed-And-Breakfast.d10021-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in New Windsor ](https://expedia.com/New-Windsor-Agritourism.d10021-aaAgritourism.Travel-Guide-Accommodation)
- [Guest Houses in New Windsor ](https://expedia.com/New-Windsor-Guest-Houses.d10021-aaGuestHouses.Travel-Guide-Accommodation)
- [Condo Rentals in New Windsor ](https://expedia.com/New-Windsor-Condos.d10021-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in New Windsor ](https://expedia.com/New-Windsor-Apart-Hotels.d10021-aaApartHotels.Travel-Guide-Accommodation)
- [Chalets in New Windsor ](https://expedia.com/New-Windsor-Chalets.d10021-aaChalets.Travel-Guide-Accommodation)
- [Inns in New Windsor ](https://expedia.com/New-Windsor-Inns.d10021-aaInns.Travel-Guide-Accommodation)
- [Hostels in New Windsor ](https://expedia.com/New-Windsor-Hostels.d10021-aaHostels.Travel-Guide-Accommodation)
- [Lodges in New Windsor ](https://expedia.com/New-Windsor-Lodges.d10021-aaLodges.Travel-Guide-Accommodation)
- [RV Parks in New Windsor ](https://expedia.com/New-Windsor-RV-Parks.d10021-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in New Windsor ](https://expedia.com/New-Windsor-Resorts.d10021-aaResorts.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in New Windsor?

### What's the top vacation rental in New Windsor?

### How many vacation rentals are there in New Windsor?

### What can I see and do in New Windsor?

### What are vacation rentals like in New Windsor?

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Activities

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Packages

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