Holiday houses in Wappinger

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Top-rated holiday rentals in Wappinger

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Guest suite in Wappingers Falls
4.83 out of 5 average rating, 128 reviews

Private ground floor guest suite in Hudson Valley

Guest favorite/newly renovated/private, ground floor guest suite. Br/full bath/large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen. Car suggested.

Top Guest favourite
A charming two-story cottage is surrounded by trees, with a lush green hillside in the backdrop. The driveway leads to a garage with two entrance doors. An outdoor staircase ascends to the living area, illuminated by dappled sunlight filtering through the leaves.
Cottage in Pawling
4.97 out of 5 average rating, 109 reviews

Forest Acres Cottage: Appalachian/Empire St Trail!

This charming, stand alone cottage was completely renovated to welcome you to the picturesque Hudson Valley. Secluded porch overlooks a peaceful forest. Fast wi-fi, high end mattresses, cozy linens, fully stocked cook's kitchen and gas stove. Located on one of the area's most scenic roads yet close to major highways, Metro-North railroad and Hudson Valley delights. Three Empire State Rail Trail and two Appalachian access points merely 5-10 minute drive. Bring your bikes and walking shoes!

Top Guest favourite
Apartment in Wappingers Falls
5 out of 5 average rating, 236 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom

Top Guest favourite
Home in New Hamburg
4.94 out of 5 average rating, 272 reviews

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.

Top Guest favourite
A spacious dining area features a large wooden table surrounded by eight chairs, situated beneath a vaulted ceiling with exposed beams. Large windows allow natural light to illuminate the space, complemented by potted plants and a cozy rocking chair positioned nearby.
Home in Marlboro
4.99 out of 5 average rating, 220 reviews

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.

Top Guest favourite
A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.
Cottage in Rhinebeck
4.93 out of 5 average rating, 332 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, comfortable bedrooms & quiet workspaces- learn more at cascadafarm.com

Top Guest favourite
A spacious bedroom features a large queen bed with a contrasting striped blanket. Nightstands are positioned on either side, and a lamp provides soft lighting. Two windows with light-filtering curtains allow natural light to fill the room, complemented by a beige carpet.
Guest suite in Marlboro
4.96 out of 5 average rating, 516 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

Guest favourite
The exterior view of a small cabin features a red siding with white trim and a welcoming front door. Two blue adirondack chairs are positioned on the porch beside a small table. A potted plant and a decorative wreath adorn the entrance.
Tiny home in Newburgh
4.9 out of 5 average rating, 707 reviews

Cabin in the heart of the Hudson Valley, Cabin 4

Our little cabin is perfect for one or two guests for short stays while visiting local family, touring the areas wineries or nature trails, or for a clean, quiet over night stop while traveling long distances. Explore the Shawangunk Wine Trail, hike Minnewaska, sip cider at Angry Orchard, visit The Walkway Over the Hudson, or sample and shop the areas diverse farm stands and breweries. There is so much to see and do in the Hudson Valley and our cabin is close to it all!

Top Guest favourite
A peaceful outdoor view showcases a well-maintained yard with lush green grass and various trees. A pathway made of stones leads to the entrance of the building, which features a covered porch under a metal roof. Sunlight filters through the surrounding foliage.
Guesthouse in Fishkill
4.91 out of 5 average rating, 122 reviews

Hudson Valley Studio in the Village of Fishkill NY

This spacious studio is in a quiet cul-de-sac and under a half mile walk from the Village of historic Fishkill, NY. Also, only a 10 minute drive to Beacon, NY! It is a private dwelling that includes a full kitchen, 1 new Queen bed, 1 new pull out bed, and a separate room for laundry. Plenty of drawers and closet place caters to up to 4 guests for whichever Hudson Valley activity you're in town for. Come enjoy the atmosphere of this Hudson Valley studio!

Top Guest favourite
The living room features two comfortable white sofas adorned with red accent pillows, positioned around a wooden coffee table. Natural light floods in through multiple windows, illuminating the space. A decorative flower arrangement sits on the table, enhancing the cozy ambiance.
Cottage in New Paltz
4.99 out of 5 average rating, 581 reviews

Stone House 1807. Comfort, Peace and Nature.

Historic 200 yr old stone cottage, on three floors, renovated to a high standard, creating a very comfortable and peaceful retreat, whilst retaining soul and character. Extreme cleanliness is a priority. Quality bedding assures a good nights sleep. The bathroom offers a rain shower and soaking tub. The kitchen is fully equipped and fresh produce is available from the neighboring organic farm in season. Good hiking trails are accessible from the house.

Top Guest favourite
The kitchen features white cabinetry with glass display doors, showcasing colorful dishware. A Viking range is prominently positioned, with a polished countertop below. A wooden table with two chairs sits on a light yellow floor, illuminated by warm lighting from a nearby lamp.
Condo in Beacon
4.99 out of 5 average rating, 635 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

Top Guest favourite
Large triangular windows provide a view of the snowy landscape outside, allowing natural light to fill the space. The wood-paneled walls and ceiling create a warm ambiance, while a minimalist chandelier hangs above, adding a touch of modern design.
Guest suite in Marlboro
4.97 out of 5 average rating, 266 reviews

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.

Popular amenities for Wappinger holiday rentals

When is the best time to visit Wappinger?

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Avg. price$300 NZD$257 NZD$254 NZD$256 NZD$257 NZD$266 NZD$303 NZD$291 NZD$266 NZD$281 NZD$256 NZD$256 NZD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Wappinger?

    Wappinger has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Wappinger?

    Experience the best of Wappinger with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Wappinger?

    Four-legged friends are welcome in Wappinger. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Wappinger?

    Yes! Work meets play with ease at over 50 vacation rentals in Wappinger featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Wappinger vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Wappinger, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Wappinger?

    Make yourself at home in Wappinger by choosing from our most frequently booked neighborhoods. We have over 40 vacation rentals in Fishkill Plains, over 30 vacation rentals in Wappingers Falls, and over 350 vacation rentals in New Hamburg.

  • Do house rentals in Wappinger have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Wappinger. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wappinger have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Wappinger. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wappinger have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Wappinger. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wappinger have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Wappinger. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Wappinger

  • Total holiday rentals

    Explore 90 holiday rentals in Wappinger

  • Nightly prices starting at

    Wappinger holiday rentals start at $68 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,540 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    80 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!

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