House holiday rentals in Wappinger

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Top-rated house rentals in Wappinger

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

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Top Guest favourite
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.

Guest favourite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock
4.94 out of 5 average rating, 379 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Top Guest favourite
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, 122 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 favourite
Home in New Hamburg
4.94 out of 5 average rating, 274 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 favourite
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
4.99 out of 5 average rating, 221 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 favourite
A serene stream cascades over smooth rocks, surrounded by a wooded area filled with autumn leaves. A wooden bench sits nearby, offering a tranquil spot to enjoy the peaceful atmosphere. The gentle flow of water reflects the greenery of the trees.
Home in Rhinebeck
4.95 out of 5 average rating, 279 reviews

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

Top Guest favourite
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, 133 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

Top Guest favourite
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring
4.95 out of 5 average rating, 355 reviews

Hilltop Hideaway Forest Villa on 13 acres!

Our artistic, spacious , comfortable home is set on 13 (fairytale-esque) private, forest acres. We are minutes away from hiking trails, swimming lakes, and the Hudson River where you can kayak. The house is located on 13 acres of land just minutes away from the vibrant shopping of downtown Cold Spring, NY. It is surrounded by lakes and hiking trails, including the Appalachian Trail. We are minutes away from the Cold Spring train station.

Guest favourite
Home in Beacon
4.92 out of 5 average rating, 165 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 favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances, including a gas stove and refrigerator. A black island is enhanced by a minimalist pendant light above, while natural light floods in through large windows, illuminating a simple green plant centerpiece.
Home in Kerhonkson
4.97 out of 5 average rating, 182 reviews

ENTER HOME - Minimalistic style warm & inviting

ENTER our HOME with an inviting comfortable setting filled with natural light and clean lines inspired by Nordic Design. Full new kitchen with all Bosch appliances including washer and dryer. Our home is designed to embrace the beautiful nature around you and to bring peace and comfort to your stay. ENTER HOME is great for individuals, couples, or families with kids. AC in both bedrooms only

Guest favourite
The architectural design is showcased at dusk, with warm light emanating from large windows. The unique geometric structure stands amidst trees, highlighting its modern features and the surrounding natural landscape.
Home in Rhinebeck
4.91 out of 5 average rating, 302 reviews

Architectural wonder in the woods

Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4! Feel free to send us a message for any requests, we love hearing from people.

Guest favourite
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?

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Avg. price$278 AUD$252 AUD$243 AUD$278 AUD$264 AUD$295 AUD$394 AUD$362 AUD$274 AUD$274 AUD$269 AUD$307 AUD
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Quick stats about house rentals in Wappinger

  • Total holiday rentals

    Explore 40 holiday rentals in Wappinger

  • Nightly prices starting at

    Wappinger holiday rentals start at $71 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Wappinger holiday 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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