
House vacation rentals in New Windsor
Find and book unique houses on Airbnb
Quick stats about house rentals in New Windsor

Total vacation rentals
Explore 10 vacation rentals in New Windsor

Nightly prices starting at
New Windsor vacation rentals start at $80 per night before taxes and fees

Verified guest reviews
Over 380 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of New Windsor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across New Windsor rentals

4.8 Average rating
New Windsor stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in New Windsor
Guests agree: these houses are highly rated for location, cleanliness, and more.

Mindful Escape: Theater, Trails, Wood Stove
Exhale and recharge in this luxurious space at the foot of the Shawangunk Mountains. This gem features an open-concept kitchen and living room, perfect for connecting with nature. Enjoy the high-end Foster Leather Sofa, cozy movie nights on a 120" projector screen, and a wood-burning stove for chilly evenings. Every detail, from fresh linens to a meaningful library, is thoughtfully curated. Discover hidden messages throughout the house, inviting you to explore and unwind in this serene retreat.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for an exciting, romantic, unique experience but can accommodate a 3rd person.

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King
Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

Charming Getaway 16mi to West Point!
3Bdr Hudson Valley Getaway with king bed and 5 other beds, your own private hot tub, and a bathroom with heated floor makes every step so cozy! The house sits on a gorgeous two acres surrounded by trees and complete with a fire pit. Fast Wi-Fi , free off street parking just 16mi to West Point. Each bedroom has it’s own desk making this a great work from home space for multiple people. - 3 bdr - 3 desks - 6 beds, 1 king, 2 queen, 1 queen sofabed, 2 twin, all with comfy hybrid gel mattresses

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Cozy Riverfront Victorian in the Hudson Valley
Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

River & Mtn Views - Jacuzzi - near Metro North
Panoramic Hudson River & Storm King Mountain views, just a 5-minute walk from train station, 3 minutes to Dia Beacon. Walk to Main Street. (Or ride one of the house bikes!) Watch the sun set over the Hudson River from the Jacuzzi (or the outdoor shower) at this prime location. My kitchen is fully equipped with more than just basics. Also, Weber grill out on the deck is hooked to gas line. Includes Linens, Towels & Toiletries. House also has Iron, Ironing Board and Hair Dryer.

Lady Montgomery
Enjoy our trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge trail to Beacon and Newburgh waterfront. Perfect for friends and couples who want to explore all that the Hudson Valley has to offer. Enjoy shopping, farms, hiking or dining. Equipped with an outdoor patio in season, fireplace, fire pit and 2 bikes. Everyone will enjoy their time in this comfortable artsy home!

Hudson Valley Hygge House~ comfort in the country!
Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

The Little Red House
Located in a quiet neighborhood just off the Hudson River, yet only a 10 min drive from the bustling town of Beacon and within walking distance to the Newburgh action where you will find restaurants, coffee shops, galleries local shopping, and nightlife. With countless hiking spots, farms, breweries, and wineries, your stay in Hudson Valley will be memorable. The house was also a filming & staging location for the movie “Adults” starring Michael Cera

Eclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC
Clean 2-story house on a residential street/safe area Free on-off street parking Eat-in kitchen Dining room Living room-fold out ottoman Free washer-dryer in utility room 2 Internet TVs, WIFI Work area Large backyard, art supplies, games, books Fire pit Community Pool closed again. Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping No river or mountain view directly from house. Airbnb threw that in.

Charming Hudson Valley Home: Minutes to West Point
Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available
Popular amenities for New Windsor house rentals
House rentals with a pool

midcentury mod hot tub*walk out trail R2R/Mohonk
Woodstock Historic Artist Estate - The Pond House

Entire Home, Private Indoor Pool

4Br Mountain Brook House on 130 acres w/ trails

Scenic River View Escape | New Paltz

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Peace & Privacy - High Falls (hot tub & salt pool)
Weekly house rentals

New Paltz Guest Cabin Nestled In The Woods

Tranquil Tree-House on the beautiful Hudson River

Panoramic Lakeviews & Lush Garden | Beach Access

Creekside cottage on 65 acres

NEW! Stylish Home in the Heart of Beacon

Cook House, Modern Cottage with Hot Tub

Accord River House

Beacon Creek House
Private house rentals

Lower Hudson Valley Idyllic Retreat

Castle View on Hudson River

Margaret's Heart

Modern 3BD West Point USMA House w/ HotTub!

River Views & Hot Tub | Riverview on Washington

Eclectic one-bedroom house

Architect's Hudson Valley Home in the Woods

Mountainside Home (Beacon/Cold Spring)
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- Times Square
- Central Park Zoo
- Hunter Mountain
- New York City Center
- Yankee Stadium
- Mountain Creek Resort
- Columbia University
- MetLife Stadium
- American Dream
- Bethel Woods Center for the Arts
- Rockefeller Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Radio City Music Hall
- Fairfield Beach
- Astoria Park
- Thunder Ridge Ski Area
- Bronx Zoo
- The Metropolitan Museum of Art
- Resorts World Catskills
- Nickelodeon Universe
- Lincoln Center For The Performing Arts
- Mohonk Preserve
- Storm King Art Center
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