
Holiday houses in Wappinger
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Wappinger
Guests agree: these stays are highly rated for location, cleanliness and more.

Hoppy Hill Farm House
Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Hudson Valley Tiny House
If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Two heating systems for the winter. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

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.

Romantic Apartment in Historic Stone Ridge
Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

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

Secluded Hilltop Cabin near Beacon & Cold Spring
3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Cozy, Small Studio with Backyard & great A/C
Cozy, small studio on quiet block. Near Main Street, Roundhouse, hiking, restaurants. Fully private space & entrance, shared backyard, new A/C, wifi. Walk everywhere. Queen-sized bed. BEFORE YOU BOOK - 200 year old house - hosts live upstairs and there is another guest apartment. You WILL NOTICE sounds from others. QUIET HOURS from 10 PM to 8 AM. As a courtesy to others, please keep conversations quiet after 10 PM. We only book guests with favorable Airbnb reviews. NO SMOKING please.

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.

Cliff Top at Turtle Rock
Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Special Nest w Private Entrance River View Porches
Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

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 like shopping, hiking or dining. Equipped with an outdoor patio, fireplace, fire pit and 2 bikes to help you explore. Everyone will enjoy their time in this comfortable artistic home!

Woodland Neighborhood Retreat
Relax in a cozy studio in the peaceful woods. Tasteful high-quality touches will have you feeling comfortable right away! This is an ideal space for up to 2 adults and up to 2 children. We live upstairs & offer self-check-in. A rare find in the Hudson Valley, our neighborhood is mostly flat, with walkable, quiet roads, and excellent bird-watching. It's an easy bike ride to connect to the vast state-wide rail trail system & all that the Mohonk Preserve has to offer.
Popular amenities for Wappinger holiday rentals
Stay near Wappinger's top sights
Other great holiday rentals in Wappinger

Ice Pond Cottage

Old Mill Cottage - Upstate Mountain Views

Beacon Hills Retreat Apartment

3000 sq ft Poughkeepsie home with chef's kitchen

Village Center Duplex

The Atala

Chez Moi-4 beds-3 bedroom-two bath-sleeps 7-

Private, spacious apartment
When is the best time to visit Wappinger?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $263 AUD | $225 AUD | $222 AUD | $224 AUD | $225 AUD | $233 AUD | $266 AUD | $255 AUD | $233 AUD | $294 AUD | $285 AUD | $242 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 |
Frequently Asked Questions
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!
How much does it cost to stay in house rentals in Wappinger?
Experience the best of Wappinger with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Wappinger have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Wappinger. Enjoy a tailored experience with all the comforts you desire.
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.
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 bed and breakfast rentals in Wappinger have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi 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.
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.
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.
Do bed and breakfast rentals in Wappinger have free parking?
Absolutely! We offer over 10 bed and breakfast 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 80 holiday rentals in Wappinger

Nightly prices starting at
Wappinger holiday rentals start at $60 AUD per night before taxes and fees

Verified guest reviews
Over 4,270 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, Wi-Fi and Pool across Wappinger rentals

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




