
House vacation rentals in Wappinger
Find and book unique houses on Airbnb
Top-rated house rentals in Wappinger
Guests agree: these houses are highly rated for location, cleanliness, and more.

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!

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.

This New House
Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

The Cozy Cape In Historic Hyde Park
Modern amenities meets early 20th century charm in our cozy, & totally renovated space situated in the hearth of the historic town of Hyde Park and adjacent to the Hudson River. Built in the 1940s, our Cozy Cape is nestled in a quiet neighborhood off of Route 9 & is central to historic sites, shopping, parks, and dining options. Our home is also minutes by car to the Culinary Institute Of America, Walkway Over The Hudson, wineries, antique shops, Marist and Vassar colleges & Town of Rhinebeck!

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.

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.

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.

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!

DeMew House in Historic Kingston
PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

Cozy Winter Upstate Cabin
Beautiful 2 bedroom/1 bath home centrally located between Woodstock and Saugerties in the gorgeous Catskill Mountains. Come for hiking, skiing, shopping and dining, it is all at your fingertips! Your home is a chic cabin situated on a large property and provides a fully stocked kitchen if you choose to cook at home, a gas grill, and fire pit in the back yard for evening enjoyment. Visit the many fun shops just down the road, or one of our lovely locally owned restaurants! Enjoy!

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.

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
Popular amenities for Wappinger house rentals
House rentals with a pool

Private Hudson Valley Country Retreat

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

Bluestone Escape - Where everyone is at home.

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

Woodstock Historic Artist Estate- The Museum House

Warm & Comfortable Family Stay nr Woodstock

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

Cozy ranch near FDR Historical Site

Caroline House Beacon Getaway

Creekside cottage on 65 acres of land

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

Architect's Hudson Valley Home in the Woods

Clove Schoolhouse on Mohonk Preserve

La Casita - Home Away From Home.

The Pudding Pad Lake House
Private house rentals

The Hudson Valley Hideaway

Welcome to Newburgh's Cozy Cove

Hudson Valley Boutique Airb&b

3000 sq ft Poughkeepsie home with chef's kitchen

Luxe Wooded Modern Getaway Retreat + Spa

Mountainside Home (Beacon/Cold Spring)

Cozy Studio in a Great Location!

Spacious. Sleeps 13 w/Pool+Hottub+Firepit+Gameroom
When is the best time to visit Wappinger?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,194 GYD | G$37,221 GYD | G$35,966 GYD | G$41,194 GYD | G$39,103 GYD | G$43,703 GYD | G$58,341 GYD | G$53,531 GYD | G$40,567 GYD | G$42,239 GYD | G$41,403 GYD | G$41,194 GYD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
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$10,455 GYD 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Pet-friendly rentals Wappinger
- Fitness-friendly rentals Wappinger
- Rentals with a patio Wappinger
- Rentals with a washer and dryer Wappinger
- Rentals with a fire pit Wappinger
- Rentals with outdoor seating Wappinger
- Family-friendly rentals Wappinger
- Rentals with a fireplace Wappinger
- House rentals Dutchess County
- House rentals New York
- House rentals United States
- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Fairfield Beach
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Mount Peter Ski Area
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Bear Mountain State Park
- Sherwood Island State Park
- Taconic State Park
- Wawayanda State Park
- Paterson Great Falls National Historical Park
- Opus 40
- Compo Beach
- Storm King Art Center
- Benmarl Winery
- Millbrook Vineyards & Winery




