
Holiday rentals in Wappinger
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Top-rated holiday rentals in Wappinger
Guests agree: these stays are highly rated for location, cleanliness 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.

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

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.

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

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

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.

Cabin in the Heart of the Hudson Valley, Cabin 1
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!

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)!

The GlassHouse: Hudson Valley Tiny Home w/Firepit
The GlassHouse is the much talked-about experience that we had crafted within a sprawling forest preserve. Its wrap-around windows allow breathtaking views to bring out the romantic in all of us! We are stone’s throw up against the Appalachian Trail right on the Dutchess/Putnam line and are less than an hour from Manhattan. Minutes from Fahnestock & Hudson Highlands State Parks & the Empire State Trail!

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.

Eagle Rock House
FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Eagle Rock 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.

Family weekend getaway
Two bedroom home located in Beacon. Mt. Views from living room and dining room windows. Close to mt. and Main st. Children welcome. Baby items available pack n play, bouncy seat, swing. Bear Mt and West Point within driving range. Extra charge for pets $100.00. Four adults or families up to 6.
Popular amenities for Wappinger holiday rentals
Stay near Wappinger's top sights
Other great holiday rentals in Wappinger

Expansive Views; Miles of River & Mountains

Life in Color, Live Art Home

2-Queen 1-Twin 2-Bath Home West Point/Low-Hud Area

Gorgeous Modern New Ranch near Rail Trail!

The cabin by the Lake! Come enjoy Candlewood Lake

Modern/lux suite on Hudson Riverfront w/views!

Cold Spring Mountain Retreat: Sun-filled Oasis

1723 Guesthouse
When is the best time to visit Wappinger?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £133 | £114 | £112 | £113 | £114 | £118 | £134 | £129 | £118 | £125 | £113 | £113 |
| 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 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 £30 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
80 of Wappinger holiday rentals include wifi 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 fireplace Wappinger
- Rentals with a washing machine and dryer Wappinger
- Rentals with a patio Wappinger
- Rentals with outdoor seating Wappinger
- House rentals Wappinger
- Pet-friendly rentals Wappinger
- Family-friendly rentals Wappinger
- Fitness-friendly rentals Wappinger
- Rentals with a firepit Wappinger
- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Fairfield Beach
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Resorts World Catskills
- Hunter Mountain Resort
- Mount Peter Ski Area
- Bash Bish Falls State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Mohawk Mountain Ski Area
- Taconic State Park
- Bear Mountain State Park
- Wawayanda State Park
- Sherwood Island State Park
- Compo Beach
- Paterson Great Falls National Historical Park
- Opus 40
- Warwick Valley Winery & Distillery
- Benmarl Winery
- Mountain Creek Water Park




