
House holiday 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.

midcentury mod * POOL * walk out trail 2 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. IN GROUND SWIMMING POOL & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 -Sept 30 HOT TUB Sept 1 - May 30

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.
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.

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.

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.

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.

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.

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

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.

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.

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.

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 house rentals in Wappinger
House rentals with a pool

Highwoods Haven | saltwater pool and hot tub

Design Farmhouse w/ Pool + Firepit | Hudson Valley

Modern Lux 5-Bed, Double Fireplace, Dogs Welcome

Cozy & Spacious Country Home - All Seasons

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Spacious Catskills Farmhouse on over 5 acres!

Peace & Privacy - High Falls (hot tub & salt pool)
Fenced & Salt Water Pool | Cozy Catskills Cottage
Weekly house rentals

The Bluff: Designer | Views | Pool | Hot Tub

Caroline House Beacon Getaway

3000 sq ft Poughkeepsie home with chef's kitchen

Luxe Wooded Modern Getaway Retreat + Spa

Chez Moi-sleeps 7-4 beds-2 bath wellness retreat

Charming home near Walkway Over The HUDSON

Mountain Top Retreat

La Casita - Home Away From Home.
Private house rentals

Immaculate Home W/ Pristine View

Mohonk Abode | dog friendly + near hiking

The "Shack" on the River

Robin's Nest Lookout: Airy Retreat w/ Scenic Pool

Huge Historic House on 10 Acres, 90 mins from City

Catskill Mountains Forest Nest for 2

Arkadia House Mid-century retreat with pool & view

Accord River House
When is the best time to visit Wappinger?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £146 | £132 | £127 | £146 | £138 | £155 | £206 | £189 | £143 | £143 | £140 | £160 |
| 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 holiday rentals
Explore 40 holiday rentals in Wappinger

Nightly prices starting at
Wappinger holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 2,260 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Wappinger holiday rentals include wifi 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
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- Rentals with a washing machine and dryer Wappinger
- Rentals with outdoor seating Wappinger
- Pet-friendly rentals Wappinger
- Rentals with a firepit Wappinger
- Fitness-friendly rentals Wappinger
- Family-friendly rentals Wappinger
- Rentals with a patio 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
- Thunder Ridge Ski Area
- Fairfield Beach
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Hunter Mountain Resort
- Mount Peter Ski Area
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Kent Falls State Park
- Mohawk Mountain Ski Area
- Taconic State Park
- Bear Mountain State Park
- Wawayanda State Park
- Compo Beach
- Sherwood Island State Park
- Paterson Great Falls National Historical Park
- Storm King Art Center
- Opus 40
- Benmarl Winery
- Mountain Creek Water Park




