
House vacation rentals in Wappinger
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Top-rated house rentals in Wappinger
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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.

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.

Beacon Creek House
Welcome to our serene oasis in Beacon, NY. If Gilmore Girls and Schitt’s Creek had a baby, it would be Beacon. Nestled beside a tranquil creek, our home features 2 cozy bedrooms, a stylish bathroom, and an open living space with a daybed. Designed with wabi-sabi aesthetics and eco-friendly materials. Just steps from Main Street and less than a 5 min drive from the train station, with scenic trails, shops and restaurants nearby. Book your stay and experience our artfully designed home and city!

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.

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 for exploring the area. Everyone will enjoy their time in this comfortable artistic home

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

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 set 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.

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!

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Welcome to Hudson Valley Hideaway — a stylish, family-friendly 4BR/2BA home tucked in the corner of Beacon just 1.5 miles from downtown & the Hudson River. Enjoy a chic living room w/ 85” TV, stocked kitchen, dining room, 1Gb WiFi, workspace & A/C. Sleep soundly in 1 King, 2 Queens & 1 Twin XL. Outside, unwind in the fenced oasis w/ pool, slide, hot tub, grill & fire pit. Modern comfort meets cozy Hudson Valley charm. SPECIAL: 20% OFF all winter stays!
Popular amenities for Wappinger house rentals
House rentals with a pool

midcentury mod * HOT TUB * walk out trail 2 mohonk

TheGoshenGetawayPoolHotTubLegoLandArcade.

Scenic River View Escape | New Paltz

Highwoods Haven | saltwater pool and hot tub

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Peaceful Light-Filled Guesthouse 1 Hour From NYC

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

4 Bd Paradise Gorgeous Design Close to All!

3000 sq ft Poughkeepsie home with chef's kitchen

Mt hikes, city strolls river walks

The Gatehouse in Historic Hyde Park

The Waterfall House

Fully stocked creekside sauna retreat with privacy

Cottage on the Creek

4BR|2Bath|King Beds|Walk to Marist|CIA|Pet|Parking
Private house rentals

The Hudson Valley Hideaway

Caroline House Beacon Getaway

Hudson Escape W/ Hot Tub + Bridge View

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

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

Beautiful Escape! Hudson Valley House

Arkadia House Mid-century retreat with pool & view

Home in Cold Spring- Farm Stay!
When is the best time to visit Wappinger?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,150 GYD | G$37,181 GYD | G$35,928 GYD | G$41,150 GYD | G$39,061 GYD | G$43,657 GYD | G$58,278 GYD | G$53,474 GYD | G$40,523 GYD | G$40,523 GYD | G$39,688 GYD | G$45,328 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$10,444 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!
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- Rentals with a patio Wappinger
- Rentals with a fireplace Wappinger
- Rentals with outdoor seating Wappinger
- Family-friendly rentals Wappinger
- Pet-friendly rentals Wappinger
- Rentals with a fire pit Wappinger
- Rentals with a washer and dryer Wappinger
- Fitness-friendly rentals Wappinger
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