Holiday Homes in New Windsor

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for New Windsor holiday homes

TV, fireplace

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

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is NZ$657
includes taxes & fees
12 May - 13 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor spa tub

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (62 reviews)
"Very good host "
United States
Binyomin
The price is NZ$847
includes taxes & fees
12 May - 13 May
Country House w/Hot Tub, Deck, Grill & Fire Pit
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is NZ$398
includes taxes & fees
13 May - 14 May
Luxury home near West Point
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (6 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is NZ$645
includes taxes & fees
12 May - 13 May
Fabulous 3bdrm Home w/parking!
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is NZ$536
includes taxes & fees
13 May - 14 May
Luxury House Near West Point
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is NZ$540
includes taxes & fees
14 May - 15 May
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Terrace/patio

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$656
includes taxes & fees
12 May - 13 May
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is NZ$252
includes taxes & fees
12 May - 13 May
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Outdoor spa tub

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
New Paltz
9.6 out of 10, Exceptional, (30 reviews)
"Excellent licatio . House was wonderful. Loved the scenery and the hot tub."
United States
Jeffrey
The price is NZ$648
includes taxes & fees
14 May - 15 May
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (37 reviews)
"House was great, it had everything we needed and even provided coffee! "
United States
Colleen E.
The price is NZ$845
includes taxes & fees
12 May - 13 May
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Interior

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks

Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
The price is NZ$1,246
includes taxes & fees
12 May - 13 May
Entire Lakeview House ~ 1 hour to MetLife ~ Hot Tub~Firepit~Stunning View~Decks
Fridge, microwave, oven, stovetop

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Warwick
10.0 out of 10, Exceptional, (5 reviews)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
The price is NZ$716
includes taxes & fees
18 May - 19 May
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (16 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is NZ$248
includes taxes & fees
12 May - 13 May
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is NZ$785
includes taxes & fees
13 May - 14 May
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is NZ$761
includes taxes & fees
31 May - 1 June
Contemporary Cozy Cottage
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (36 reviews)
"Awesome place, great location. We loved our stay."
United States
Will R.
The price is NZ$334
includes taxes & fees
17 May - 18 May
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Interior

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (12 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is NZ$1,151
includes taxes & fees
13 May - 14 May
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Interior

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
10.0 out of 10, Exceptional, (2 reviews)
"Great host"
United States
Lindsey F.
The price is NZ$853
includes taxes & fees
12 May - 13 May
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Interior

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

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 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
Briana T.
The price is NZ$732
includes taxes & fees
27 May - 28 May
Lovely 3BR Home with parking-Walk to WP Gate!
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
The price is NZ$254
includes taxes & fees
12 May - 13 May
Glamping Tent & Campsite by Minnewaska State Park
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 New Windsor Hotel Reviews

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

2/10 Terrible
"I've had such an awful experience with this hotel that I will never again stay at a building with "Fairfield" in the name. I booked this hotel in part because they had a pool, and did not see anything in the app about it only being open seasonally. When we arrived, we found out the pool was closed. We checked out without a half hour or so, but they would not refund our stay. I reached out to the manager, and she refused to refund the night because the hotel was fully booked. (Be that as it may, rooms were still available that night on the app). "
Anthony 2-night trip
Posted 4 hours ago
Fairfield Inn & Suites by Marriott Goshen Middletown

Find out more about New Windsor

New Windsor Holiday Homes information

Number of reviews
368
Accommodation
369 Holiday Homes
Lowest Price
NZ$248
Highest Price
NZ$1,246