
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.
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Other great holiday rentals in Wappinger
Top guest favourite

Home in Millerton
4.97 out of 5 average rating, 183 reviewsVacation Home In Millerton
BettyRating, 5 stars1 week ago
We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!
Guest favourite

Chalet in Hunter
4.98 out of 5 average rating, 153 reviewsTHE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
CarmenRating, 5 stars2 weeks ago
The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.
Guest favourite

Home in Hunter Mountain, Hunter
4.96 out of 5 average rating, 104 reviewsPrivate Mountain Lodge, 10mins to Hunter & Windham
PaulRating, 5 stars2 months ago
My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.
Superhost

Apartment in Vernon Township
4.73 out of 5 average rating, 112 reviews200 yds Minerals - great for hotel weddings
CindyRating, 5 stars4 days ago
The place was great and just as pictured/described. Joann gave great instructions and was very responsive. We were only there for a short stay for a race, but it looked like a great area I would’ve loved to explore if we had more time. The only thing I didn’t care for was the requirement for to wash and dry all towels before leaving. Since I already paid a hefty cleaning fee that seemed like a bit much. And the washer/dryer is small so this took a couple of loads to get done.
Guest favourite

Cottage in Greenwood Lake
4.96 out of 5 average rating, 48 reviews5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski
JasonRating, 5 stars2 weeks ago
We had a great time at Carmine's place, highly recommend.
Guest favourite

Cabin in Shandaken
4.99 out of 5 average rating, 104 reviewsA Place Called Home in The Catskill
KateRating, 5 stars1 month ago
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!
Guest favourite

Home in Tannersville
4.93 out of 5 average rating, 28 reviewsLuxury Spacious Private Home w/tub! Enjoy Spring
SantiagoRating, 5 stars2 months ago
It’s a fantastic place to stay—a well-designed, private home with a great layout. Conveniently located near the mountain, it’s perfect for skiing while still offering a peaceful retreat.
Superhost

Chalet in Fleischmanns
4.73 out of 5 average rating, 158 reviewsSauna equipped Belleayre Cozy Cabin
ChloeRating, 5 stars2 months ago
Perfect for a ski weekend. Sauna is great, and location cannot be beat.
Quick stats about holiday rentals in Wappinger
Total rentals
80 properties
Nightly prices starting at
£23 before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
- Hudson Valley Holiday rentals
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- House rentals Wappinger
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- Rentals with outdoor seating Wappinger
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- Rentals with a washing machine and dryer Wappinger
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- Family-friendly rentals Wappinger
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- Hunter Mountain
- Fairfield Beach
- Rye Beach
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Rye Playland Beach
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Rye Town Beach
- Seaside Beach
- Resorts World Catskills
- Jennings Beach
- Taconic State Park
- Ringwood State Park
- Rockland Lake State Park
- Marvin Beach
- Walkway Over the Hudson State Historic Park
- Thunder Ridge Ski Area
- Calf Pasture Beach
- Mohawk Mountain Ski Area
- Brotherhood, America's Oldest Winery
- The Ridgewood Country Club
- Hook Mountain State Park