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House vacation rentals in Wappinger

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Top-rated house rentals in Wappinger

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Top guest favorite

An outdoor area features a spacious in-ground swimming pool surrounded by a well-maintained lawn. Comfortable lounge chairs are positioned nearby, offering a relaxing space in the shade of lush greenery. Tall trees provide privacy and a natural feel to the setting.

Home in New Paltz

4.98 out of 5 average rating, 497 reviews

midcentury mod * POOL * walk out trail to mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village Several outdoor seating areas. THE WHOLE PLACE IS YOURS FULL PRIVATE ACCESS HOUSE, POOL & PROPERTY POOL OPEN 5/1 - 9/30

Top guest favorite

A modern living area features a gray sofa with tufted seating, positioned near a wooden coffee table. Exposed wooden beams span the ceiling, while a cozy rattan chair adds warmth. Natural light streams through windows, creating a bright and airy ambiance.

4.99 out of 5 average rating, 142 reviews

NEW! Stylish Home in the Heart of Beacon

This Scandinavian style home in the heart of Beacon is bright, airy and modern with beautifully-restored architectural details. Located on a quaint street in the best part of town just steps away from the Roundhouse and Main Street. Enjoy the brewery, bars, restaurants, shops, galleries, and so much more - all within walking distance. Every piece of furniture and decor was handpicked to provide you the perfect designer-quality getaway, focusing on natural simplicity with contemporary luxuries.

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, 228 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.

The historic family home is set on a neatly manicured hill, surrounded by lush greenery. The two-story structure features large windows and a welcoming porch, while the expansive lawn offers ample outdoor space for relaxation. Bright sunlight enhances the inviting atmosphere.

4.75 out of 5 average rating, 179 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 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, 205 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

The open living space features a large wooden table at its center, surrounded by chairs. Floor-to-ceiling windows flood the area with natural light, offering views of the outdoors. Recessed lighting and plants accentuate the high ceilings and triangular architecture.

4.97 out of 5 average rating, 398 reviews

River & Mtn Views - Jacuzzi - near Metro North

Panoramic Hudson River and 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 go down 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.

A spacious main room features barn-like vaulted ceilings with exposed beams and polished concrete floors. Modern kitchen appliances and cabinetry are complemented by a large L-shaped sofa adorned with pillows. A ping pong table is present, and large windows provide views of the surrounding forest.

Home in New Paltz

4.95 out of 5 average rating, 150 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

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

4.99 out of 5 average rating, 110 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

The exterior of a modern home is shown, surrounded by a lush, green lawn and trees in the background. The structure exhibits a mix of large windows and unique architectural elements, including a cylindrical section. A stone path leads to the entrance, adding character to the landscape.

Home in Wappingers Falls

4.9 out of 5 average rating, 112 reviews

LivingUPstation

Sustainable living Upstate NY. The space is the outcome of 10 years of reclaiming materials from various construction projects in NYC. A true example of mid century modern architecture is converted to a sanctuary with a 3 way open wood burning fireplace and Finnish indoor sauna looking at nature less than 90 mins by train from Grand Central. The space introduces guests to unique woodworking and art a few minutes away from great nature escapes, fine dining and Dia Beacon.

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

4.87 out of 5 average rating, 103 reviews

Lady Montgomery

Enjoy this trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge and Newburgh waterfront. Perfect for friends and couples who want to explore all the Hudson Valley has to offer like shopping, hiking or dining. Equipped with an outdoor patio, fire pit and two bikes to help you explore the surrounding areas. Everyone will enjoy their time in this comfortable artistic home.

Top guest favorite

A serene sunset view over the Hudson River is captured, with vibrant colors reflecting on the water. Silhouetted trees frame the scene, highlighting the natural beauty of the landscape as clouds drift through the colorful sky.

Home in Wappingers Falls

4.93 out of 5 average rating, 227 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. 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.

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, 162 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.

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Popular amenities for Wappinger house rentals

Free parking on premises

Air conditioning

House rentals with a pool

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

4.86 out of 5 average rating, 163 reviews

Scenic River View Escape | New Paltz

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4.88 out of 5 average rating, 150 reviews

4Br Mountain Brook House on 130 acres w/ trails

A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.

Home in Stamford

4.96 out of 5 average rating, 252 reviews

Midcentury Modern ZenHouse Sculptor Studio

An aerial view captures a stylish retreat surrounded by lush greenery. A wooden deck outlines a rectangular saltwater pool, accompanied by lounge chairs and large umbrellas. A shaded seating area is positioned nearby, promoting outdoor relaxation.

Home in Kerhonkson

4.93 out of 5 average rating, 121 reviews

Modern Lux 5-Bed, Pool Open! Dogs Welcome

Top guest favorite

A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.

Home in Pound Ridge

5 out of 5 average rating, 166 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

4.91 out of 5 average rating, 101 reviews

Stylish Woodstock Pool Home

The spacious backyard features a well-maintained in-ground pool surrounded by lush green grass. Comfortable lounge chairs are positioned on the deck and by the pool. A slide is present for added fun, while the home is partially visible with an elevated deck overlooking the area.

4.92 out of 5 average rating, 139 reviews

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

An inviting in-ground saline pool is surrounded by lush greenery and trees. Sun loungers are placed nearby on a spacious patio, providing a serene outdoor space for relaxation. The pool area is framed by a well-maintained lawn and natural landscaping.

Home in Cottekill

4.95 out of 5 average rating, 277 reviews

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

Weekly house rentals

Top guest favorite

A spacious living area is presented with a large sectional sofa and a decorative area rug. Natural light enters through multiple windows, illuminating the room. A wooden sideboard and a modern television are positioned against the wall, complemented by potted plants for a touch of greenery.

Home in Fishkill

5 out of 5 average rating, 15 reviews

Ice Pond Cottage

An entertainment area is displayed with a wall-mounted television above a sleek console. A decorative lamp and a wooden sculpture add warmth. A serving tray with glasses and an ice bucket is positioned nearby, along with a board game for casual gatherings.

Home in Highland

4.88 out of 5 average rating, 48 reviews

Hudson Valley Boutique Airb&b

A modern cabin features a dark wooden exterior and large glass windows allowing natural light to fill the interior. A welcoming deck is furnished with chairs, surrounded by lush greenery and mature trees, creating a peaceful and inviting outdoor space.

Home in Pleasant Valley

5 out of 5 average rating, 31 reviews

The Wildflower House

Top guest favorite

A rustic cabin is nestled among lush greenery, featuring a screened-in porch with a staircase leading up to it. Stone steps are visible at the entrance, with a small garden area surrounding the base. The cabin blends with its natural surroundings.

Home in Cold Spring

4.89 out of 5 average rating, 46 reviews

Cabin with a View

Top guest favorite

A warmly lit living room features a navy blue sofa and two tan armchairs arranged around a patterned area rug. Floor-to-ceiling windows allow natural light to fill the space, while a stylish kitchen with bar stools is visible in the background.

Home in Fishkill

5 out of 5 average rating, 41 reviews

Chez Moi-4 beds-3 bedroom-two bath-sleeps 7-

Top guest favorite

An open-concept living space features high wooden beam ceilings and a stone fireplace. Large windows provide ample natural light and scenic views of the lake. A staircase leads to an upper level, while a cozy seating area is arranged nearby, emphasizing relaxed living.

Home in Putnam Valley

5 out of 5 average rating, 14 reviews

Dr. Ruth’s Serene Lake Retreat

Top guest favorite

The exterior of the home displays a unique design with a combination of wood paneling and large windows. The entrance is accentuated by a welcoming porch and modern railing, while a circular structure rises above, creating visual interest. A paved driveway leads to a two-car garage.

Home in Newburgh

4.97 out of 5 average rating, 58 reviews

House of Cascade - One of a Kind stay w/ hot tub

Top guest favorite

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

5 out of 5 average rating, 69 reviews

Accord River House

Private house rentals

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

4.95 out of 5 average rating, 60 reviews

Mindful Escape: Theater, Trails, Wood Stove

The spacious living room features high cathedral ceilings with large A-frame windows that provide abundant natural light. A cozy fireplace is positioned beneath a wall-mounted TV. Warm wood flooring complements the inviting atmosphere, creating a perfect space for relaxation and gathering.

Home in Carmel Hamlet

4.85 out of 5 average rating, 46 reviews

Dog & Family Friendly A-Frame - Private and Cozy

An inviting inground pool is surrounded by a wooden fence and shaded by lush trees. Several lounge chairs are positioned on the deck, and a colorful inflatable ring floats in the water, offering a serene outdoor space for relaxation.

Home in Hopewell Junction

5 out of 5 average rating, 22 reviews

MCM in the Hudson Valley

A serene deck space surrounded by lush greenery, featuring two black wicker chairs with blue cushions. A vibrant blue rug lays on the dark wood floor, and string lights hang above, adding a soft glow to the natural setting.

Home in Arlington

4.87 out of 5 average rating, 31 reviews

The Cherry House

Top guest favorite

A charming home nestled among trees features a spacious front porch adorned with planter boxes. Lush greenery and colorful flower beds surround the property, and a large boulder adds a natural element to the landscape.

Home in Cold Spring

5 out of 5 average rating, 46 reviews

Home in Cold Spring- Farm Stay!

The exterior of a charming three-bedroom home is visible, surrounded by lush greenery and mature trees. A spacious deck extends from the second floor, while a stone wall delineates the yard. The natural landscape contributes to the tranquil setting of the property.

Home in Cold Spring

5 out of 5 average rating, 9 reviews

Cold Spring Cottage

A modern entryway is framed by a glass door, leading into a space with a natural wood wall. A sculptural black chair, accented with a soft fur throw, invites relaxation. Light grey flooring complements the minimalist aesthetic.

Home in Kerhonkson

5 out of 5 average rating, 6 reviews

Hill Studio | A Creative Loft in the Sky

A contemporary house is positioned among lush greenery on a sloping lawn. The structure features large windows and a spacious front deck, while a gentle rise of grass leads to the entrance, creating a welcoming and open feel.

Home in Newburgh

4.97 out of 5 average rating, 64 reviews

Hudson Valley Escape with Hot Tub & Stunning View

Quick stats about house rentals in Wappinger

Total rentals
40 properties
Nightly prices starting at
R709 ZAR before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore