
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.

Quiet Studio Apartment in Pawling
For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

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

Hudson Valley Hideout - In the middle of it all!
Welcome to our charming 3-bedroom, 1-bath apartment, perfect for your next getaway or extended stay. Nestled in a private setting, this home offers peace and quiet with unlimited off-street parking for your convenience. Enjoy the spacious, fully fenced yard, perfect for pets to roam freely. Inside, you’ll find cozy, well-appointed bedrooms and a comfortable living space. Pet-friendly and ideal for families or small groups, this home provides all the essentials for a relaxing stay. Book today!

Secluded Hilltop Cabin near Beacon & Cold Spring
3 private acres atop small mountain. Feels like your 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!

Unwind in a Bespoke Downtown Studio W Laundry
A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

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 Studio in Historic home, near Metro North
1st floor studio apartment in a private home. Located in the historic Mt Carmel/Little Italy section of Poughkeepsie. 5 minute walk to Metro North train station and entrance to the Walkway over the Hudson. Many restaurants, coffee/pastry shops within walking distance. There is off street parking and a lovely yard in back. Convenient to Marist College, Vassar College, the CIA, FDR home , Vanderbilt Mansion, Locust Grove, breweries, Rail trails and Wineries. NO third party booking allowed.

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.

Village Center Duplex
Newly renovated 2-bedroom, 1-bathroom apartment nestled in the heart of the charming village of Wappingers, New York. This inviting space offers the perfect blend of modern comfort and convenient village living, providing you with an exceptional getaway. As you step into the apartment, you will have to go up one flight of stairs before you'll be greeted by a thoughtfully designed interior that reflects both style and functionality. Located walking distance to restaurants and bars.

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!
Popular amenities for Wappinger holiday rentals
Other great holiday rentals in Wappinger

SmallRoom in HudsonValleyFarmhouse

Cozy Private Room & Private Bath in Hudson valley

Bold & Cozy Hudson Valley Getaway w/King Bed

Billie's Room in Beacon 1794 Home Walk 2 Train

Top Side

Modern Escape in Wappinger Falls

Private Room With Private Entrance

Hudson Pond · Hideaway King Suite
When is the best time to visit Wappinger?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $306 NZD | $263 NZD | $259 NZD | $261 NZD | $263 NZD | $272 NZD | $315 NZD | $313 NZD | $299 NZD | $343 NZD | $333 NZD | $282 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 holiday rentals in Wappinger
 - Total holiday rentals- Explore 80 holiday rentals in Wappinger 
 - Nightly prices starting at- Wappinger holiday rentals start at $70 NZD 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! 
Destinations to explore
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- Rentals with outdoor seating Wappinger
- Fitness-friendly rentals Wappinger
- Family-friendly rentals Wappinger
- Rentals with a fireplace Wappinger
- Rentals with a washing machine and dryer Wappinger
- Rentals with a patio Wappinger
- House rentals Wappinger
- Pet-friendly rentals Wappinger
- Rentals with a fire pit Wappinger
- Hunter Mountain
- Mountain Creek Resort
- Fairfield Beach
- Rye Beach
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Rowayton Community Beach
- Rye Playland Beach
- Resorts World Catskills
- Bash Bish Falls State Park
- Jennings Beach
- Kent Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Seaside Beach
- Walkway Over the Hudson State Historic Park
- Ringwood State Park
- Catamount Mountain Ski Resort
- Sherwood Island State Park
- Rye Town Beach
- Glen Island Beach
- Rockland Lake State Park
- Wawayanda State Park
