
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.

Lux Bungalow on the Lake
Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.
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.

Mindful Escape: Theater, Trails, Wood Stove
Exhale and recharge in this luxurious space at the foot of the Shawangunk Mountains. This gem features an open-concept kitchen and living room, perfect for connecting with nature. Enjoy the high-end Foster Leather Sofa, cozy movie nights on a 120" projector screen, and a wood-burning stove for chilly evenings. Every detail, from fresh linens to a meaningful library, is thoughtfully curated. Discover hidden messages throughout the house, inviting you to explore and unwind in this serene retreat.

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.

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 trail to Beacon and Newburgh waterfront. Perfect for friends and couples who want to explore all that 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

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!

3 BR|CIA|Marist|King Beds|Pets|Cable| Wifi
The whole group will enjoy easy access to everything from this centrally located home. Ample space inside and out for creativity, relaxing and enjoying! Located in a quiet, residential, family-oriented neighborhood. This retreat is less than 1 mile from Marist College, and the Walkway Over the Hudson. A ten-minute drive to The Culinary, Vassar College and all FDR historic sites/attractions. Also, enjoy 125 cable and Roku tv Channels. Make this home your home away from home!

Poughkeepsie 3br home near Vassar college/hospital
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.

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.
Popular amenities for Wappinger house rentals
House rentals with a pool

Private Hudson Valley Country Retreat

Entire Home (private pool), Event Friendly

4Br Mountain Brook House on 130 acres w/ trails

Scenic River View Escape | New Paltz

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Upstate Modern Scandinavian Barn in the Catskills

Cozy & Spacious Country Home - All Seasons

Hudson River views with pool and hot tub
Weekly house rentals

Ice Pond Cottage

Caroline House Beacon Getaway

3000 sq ft Poughkeepsie home with chef's kitchen

Luxe Wooded Modern Getaway Retreat + Spa

Dutchess Chalet - Hudson Valley Home w/ Hot Tub!

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

Hamptons on the Hudson: Pool, SPA, BBQ, Views!

Chez Moi-4 beds-3 bedroom-two bath-sleeps 7-
Private house rentals

Private retreat on 12 acres w hot tub and bbq

Dog & Family Friendly A-Frame - Private and Cozy

Central Beacon Retreat: Hot Tub & Chef's Kitchen

Beautiful guest house/retreat space w private LAKE

Slice of Paradise in the Country

The Gîte - Hudson Valley Retreat

Mountain View Escape

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 | $349 NZD | $315 NZD | $305 NZD | $349 NZD | $331 NZD | $370 NZD | $494 NZD | $454 NZD | $344 NZD | $358 NZD | $351 NZD | $349 NZD |
| 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 NZD per night before taxes and fees

Verified guest reviews
Over 2,160 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 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, Wi-Fi and Pool across Wappinger rentals

4.9 Average rating
Wappinger stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a washing machine and dryer Wappinger
- Rentals with a patio Wappinger
- Rentals with outdoor seating Wappinger
- Fitness-friendly rentals Wappinger
- Pet-friendly rentals Wappinger
- Family-friendly rentals Wappinger
- Rentals with a fire pit Wappinger
- Rentals with a fireplace Wappinger
- House rentals Dutchess County
- House rentals New York
- House rentals United States
- Hunter Mountain
- Mountain Creek Resort
- Fairfield Beach
- Rye Beach
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Resorts World Catskills
- Rye Playland Beach
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Jennings Beach
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Seaside Beach
- Ringwood State Park
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Sherwood Island State Park
- Glen Island Beach
- Rye Town Beach
- Rockland Lake State Park
- Wawayanda State Park
- Taconic State Park




