House vacation rentals in Wappinger

Find and book unique houses on Airbnb

Quick stats about house rentals in Wappinger

  • Total vacation rentals

    Explore 40 vacation rentals in Wappinger

  • Nightly prices starting at

    Wappinger vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Wappinger vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wappinger rentals

  • 4.8 Average rating

    Wappinger stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated house rentals in Wappinger

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.
Home in Rhinebeck
4.98 out of 5 average rating, 123 reviews

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

Top guest favorite
An open living space features a Foster Leather sectional sofa positioned around a central coffee table. Natural light streams in from a large window, illuminating the wood-burning stove nearby. A cozy area rug adds texture to the floor, creating an inviting atmosphere.
Home in Gardiner
4.97 out of 5 average rating, 159 reviews

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.

Guest favorite
A spacious living area features a light-colored couch alongside a round coffee table. Sliding doors provide separation from the sleeping area, which contains a large bed dressed in light linens. Natural light filters through the nearby windows, illuminating the warm wooden floor.
Home in Milton
4.76 out of 5 average rating, 191 reviews

Historic 1 BR Family Home Near Buttermilk Falls

This historic upstate New York family home was lovingly restored by 4th generation owners. Once a 1790 Stagecoach Stop, this 1 BR home is now the perfect stay for guests visiting Buttermilk Falls Resort & Spa, coming for a wedding in the Hudson Valley, or exploring local agritourism. Enjoy our large kitchen and sitting area, 180-degree sunroom, and newly-renovated bathroom. Our home is a duplex that sits on 5 wooded acres, and the other side of the home is also available for rent on AirBnB.

Top guest favorite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 125 reviews

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE 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 a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Top guest favorite
Home in Marlboro
4.99 out of 5 average rating, 221 reviews

Hudson Valley Farmhouse | Winery & Hiking Getaway

Tucked into the Hudson Valley, our restored 1873 farmhouse is made for slow mornings, fresh coffee, and easy weekends between hiking trails and nearby wineries 🌿 This is a private 3BR/2.5 bath first-floor unit within a shared home. Designed for a calm, quiet stay. Only registered guests are permitted on the property. Located in Marlboro near Beacon, New Paltz, Kingston West Point, Vassar, Marist, Warwick & Wallkill with a garden to enjoy and harvest fresh herbs and seasonal vegetables.

Top guest favorite
Home in New Hamburg
4.94 out of 5 average rating, 279 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door. We have added a separate kitchenette additional crockpot and induction cooktop.

Top guest favorite
A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.
Home in Kingston
4.98 out of 5 average rating, 163 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Top guest favorite
A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.
Home in Livingston Manor
4.96 out of 5 average rating, 412 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Guest favorite
Home in Beacon
4.92 out of 5 average rating, 166 reviews

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

Welcome to Hudson Valley Hideaway — a Modern stylish family friendly home in Beacon, NY, just 1.5 miles from downtown and the train. Bright, stylish home with 4 bedrooms, w/ 1 King bedroom, 2 queens and a Twin XL, stocked kitchen, and cozy living spaces. Enjoy a private fenced backyard retreat with pool, hot tub, fire pit, and grill. Perfect for relaxing or exploring the Hudson Valley, with easy access to Route 84 and local attractions.

Guest favorite
A bright living room features high ceilings and large windows, providing natural light and views of the surrounding trees. Stylish designer furniture, including two armchairs and a dark sofa, complements a geometric artwork on the wall. A textured area rug enhances the space.
Home in Wallkill
4.87 out of 5 average rating, 142 reviews

Modern Upstate Gem Surrounded by Trees | Hot Tub

Newly renovated 2.5 BR home in a forest like setting. All brand new beds, bedding and designer furniture. An outdoor fire-pit, BBQ, and space to lay on a garden blanket. Lounge in the spacious living room with high ceilings looking out at the garden and trees. Relax in a hot tub during the winter season and summer. Hiking trails nearby. Short drive to Beacon, Cold Spring, Storm King Art Center, Dia Beacon.

Top guest favorite
A mid-century octagonal house is surrounded by lush greenery, featuring large glass windows that offer generous natural light. A wooden deck extends from the entry, framed by a black railing. The serene hilltop location provides a peaceful retreat in nature.
Home in New Windsor
4.92 out of 5 average rating, 144 reviews

View House

Magnificent views from this fully renovated octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city.

Guest favorite
A serene bedroom features a metal bed dressed in floral bedding and a decorative blue pillow. Natural light brightens the room through a window with light curtains. A small plant is placed on a stand beside the bed, while a vintage dresser and a mirror are positioned against the wall.
Home in Highland
4.87 out of 5 average rating, 115 reviews

Serene & Spacious Getaway

A relaxing escape from city life in the Hudson Valley. Clean and simple home on a lush acre of secluded land. Tucked away in a culdesac in one of Highland's loveliest neighborhoods, this place is a short drive from restaurants, wineries, orchards, hiking and more.

Popular amenities for Wappinger house rentals

When is the best time to visit Wappinger?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,212 GYDG$37,237 GYDG$35,982 GYDG$41,212 GYDG$39,120 GYDG$43,722 GYDG$58,366 GYDG$53,554 GYDG$40,584 GYDG$40,584 GYDG$39,747 GYDG$45,396 GYD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C
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