
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.

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.

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

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

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.

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

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.

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
House rentals with a pool

Woodstock Family Home w/ Tree House + Heated Pool

midcentury mod * POOL * walk out trail 2 mohonk

Scenic River View Escape | New Paltz

Highwoods Haven | saltwater pool and hot tub

Design Farmhouse w/ Pool + Firepit | Hudson Valley

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Cozy & Spacious Country Home - All Seasons

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

The "Shack" on the River

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

Contemporary Hudson Valley home

Rustic Swedish Barn/Featured in Airbnb Magazine
Private house rentals

Hudson Valley Luxe Retreat w/ Hot Tub, Pool & Gym!

Private retreat on 12 acres w hot tub and bbq

Mohonk Abode | dog friendly + near hiking

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

Dutchess Chalet - Hudson Valley Home w/ Hot Tub

Huge Historic House on 10 Acres, 90 mins from City

Home in Cold Spring- Farm Stay!

Hyde Park Luxury A-Frame - Pool/Chef Kitchen
When is the best time to visit Wappinger?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| 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 $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!
Destinations to explore
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- Rentals with a washing machine and dryer Wappinger
- Fitness-friendly rentals Wappinger
- Rentals with a patio Wappinger
- Pet-friendly rentals Wappinger
- Rentals with a fireplace Wappinger
- Rentals with outdoor seating Wappinger
- Family-friendly rentals Wappinger
- Rentals with a fire pit Wappinger
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