House vacation rentals in Wappinger

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Top-rated house rentals in Wappinger

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Top guest favorite
A cozy living area is presented, featuring a soft beige sofa and a light armchair beside a wooden coffee table. A green plant adds a natural touch, and a light fixture hangs from the ceiling, while soft light filters in from a nearby window.
Home in Beacon
5 out of 5 average rating, 127 reviews

Beacon Creek House

Welcome to our serene oasis in Beacon, NY. If Gilmore Girls and Schitt’s Creek had a baby, it would be Beacon. Nestled beside a tranquil creek, our home features 2 cozy bedrooms, a stylish bathroom, and an open living space with a daybed. Designed with wabi-sabi aesthetics and eco-friendly materials. Just steps from Main Street and less than a 5 min drive from the train station, with scenic trails, shops and restaurants nearby. Book your stay and experience our artfully designed home and city!

Guest favorite
A charming two-story house is featured with a light yellow facade and white trim. A welcoming front porch with a bench overlooks the neatly landscaped yard, filled with greenery and flower beds. The inviting entrance is flanked by large windows and decorative shutters.
Home in Newburgh
4.86 out of 5 average rating, 124 reviews

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, fireplace, fire pit and 2 bikes to help you explore the area. Everyone will enjoy their time in this comfortable artistic home

Top guest favorite
A charming two-story house features warm wooden siding and multiple red window accents. A welcoming front porch is adorned with lights, complemented by a gently sloped pathway leading up to the entrance, surrounded by lush greenery and seasonal foliage.
Home in New Paltz
4.96 out of 5 average rating, 273 reviews

Eclectic one-bedroom house

This bohemian New Paltz house is 1/3 mi to Main St New Paltz, 2/3 mi to SUNY and 1 1/2 blocks from the New Paltz-Kingston rail trail. Rent entire house with a private bathroom, large deck space with table and grill, small living and dining room, EV charging and a kitchen. The entire upstairs is a spacious and unique bedroom space. Walking distance to many restaurants and bars. New Paltz is a central location for outdoor fun, close to Mohonk, the Gunks, great biking, hiking, rock climbing, etc.

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, 189 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, 114 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 Wappingers Falls
4.94 out of 5 average rating, 267 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 spacious dining area features a large wooden table surrounded by eight chairs, situated beneath a vaulted ceiling with exposed beams. Large windows allow natural light to illuminate the space, complemented by potted plants and a cozy rocking chair positioned nearby.
Home in Marlboro Township
4.99 out of 5 average rating, 218 reviews

Historic 1873 Farmhouse Near Vineyards & Orchards

Come relax at our lovingly restored historic 1873 Marlboro Farmhouse, centrally located between Beacon, New Paltz, Kingston, and West Point; and close to many local farms, orchards, wineries, and fantastic hiking trails. The farmhouse is split into three separate and private units. This listing is for the spacious 3400 sq. ft 3 BR/2.5 bath unit that occupies the entire first floor. This is NOT a party house. The only guests allowed on the property are the ones listed on the reservation.

Top guest favorite
Home in New Paltz
4.95 out of 5 average rating, 173 reviews

New Paltz Guest Cabin Nestled In The Woods

Newly renovated, modern, guest house located on 20 acres of a private estate at the base of the Gunks. This private, fully renovated 1 bed/1 bath is the perfect retreat. Located a short scenic drive from Minnewaska State Park (8 mins), Mohonk Preserve (5 mins) & New Paltz Main Street (15 mins). Centrally located for easy access to many trails, orchards, wineries, farm stands, swimming holes and lakes. Also easy access to Stone Ridge, High Falls, Rosendale, Kingston, Woodstock & Hudson.

Top guest favorite
Home in Poughkeepsie
4.95 out of 5 average rating, 130 reviews

The Atala

The Atala is a two story 3BR/2Bath house, nestled in a quiet neighborhood close to the city's excitement and attractions. Warm up by the fireplace in the living room while watching your favorite shows on a 75” flat screen TV, or brew a cup of coffee in our convenient coffee bar. Enjoy three inviting bedrooms with air conditioning/heating and a fully equipped kitchen. Our backyard with furniture, fire pit, and gas grill, is perfect for relaxing with family and friends.

Top guest favorite
A spacious living area features large windows allowing ample natural light. A gray sectional couch is complemented by a mustard yellow chair and a round ottoman. Wooden flooring is contrasted by a blue area rug, adding warmth to the minimalist design.
Home in Newburgh
4.99 out of 5 average rating, 184 reviews

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

Top guest favorite
A charming two-story house features a combination of red siding and stone accents. A welcoming porch with white railings leads to the front door. Lush greenery surrounds the entrance, enhancing the inviting exterior. Nearby, a well-maintained lawn adds to the home's appeal.
Home in Newburgh
4.99 out of 5 average rating, 131 reviews

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

Superhost
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, 136 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.

Popular amenities for Wappinger house rentals

When is the best time to visit Wappinger?

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Avg. priceﺩ.ﺇ723ﺩ.ﺇ654ﺩ.ﺇ632ﺩ.ﺇ723ﺩ.ﺇ687ﺩ.ﺇ768ﺩ.ﺇ1,025ﺩ.ﺇ940ﺩ.ﺇ712ﺩ.ﺇ712ﺩ.ﺇ698ﺩ.ﺇ797
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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 ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 2,240 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!

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