
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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Popular amenities for Wappinger holiday rentals
Other great holiday rentals in Wappinger
Top guest favourite

Home in Fishkill
5 out of 5 average rating, 11 reviewsIce Pond Cottage
ChelseaRating, 5 stars1 week ago
Linda’s place was quiet and in a beautiful location. Plenty of space for one couple and two single ladies (having a futon was awesome). Everything was clean and Linda was super helpful. Would highly recommend. Great for a bethel trip.
Guest favourite

Flat in Marlboro Township
4.82 out of 5 average rating, 73 reviewsSpectacular Log Home Estate North Wing Apt
NatashaRating, 5 stars2 weeks ago
Quick to respond to any questions. Beautiful, safe property.
Top guest favourite

Flat in Fishkill
4.98 out of 5 average rating, 50 reviews1 Bedroom Apartment on Main St.
ChrisRating, 5 stars2 weeks ago
A charming place that had everything I needed! The bed was comfortable, the place was clean, and the host was hospitable. And I always appreciate coffee and tea options, with half and half in the refrigerator! I would stay here again.

Home in Wappingers Falls
Robin's Nest Lookout: Airy Retreat w/ Scenic Pool
DeannaRating, 5 stars2 weeks ago
My family & I stayed here for 5 nights in May/June 2025. We came for a funeral, to visit with family & friends & to spend one day in NY City. Our bunch of eight consisted of ages 16-77. There was plenty of room to spread out between the fully finished basement, main floor and upstairs bedrooms. There were two full bathrooms upstairs & one ½ bath on the main floor. The beds were comfortable; the oversized sectionals were super cozy. The kitchen was fully stocked & had extra things available like Ziploc bags of different sizes. I always forget to buy those for leftovers when we buy groceries. The house sits high up on a hill, has a nice view & is in a quiet neighborhood. We enjoyed our morning walks in the hood. It was a bit chilly during our stay, so we could not make use of the deck and pool, but it looked inviting. The main living room was a great place for us to come together and play games or watch TV. I don’t have any complaints. I highly recommend Robins Nest! Thank you

Farm stay in Marlboro Township
5 out of 5 average rating, 3 reviewsGallery On The Pond
DanaRating, 5 stars1 month ago
Shula's home on the pond is a gem of a sanctuary. Peaceful and quaint outside the city life. She hosted a lovely place to stay and I would definitely return and recommend to others. This place is the perfect homestead to unwind and enjoy nature as I sat outside watching birds , rabbits, geese and beavers each morning over coffee. Thanks so much for my relaxing weekend.
Guest favourite

Flat in Fishkill
4.77 out of 5 average rating, 13 reviewsPrivate, spacious apartment
TahnyaRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ 5/5 – A Perfect Stay! I had an absolutely fantastic experience!! From the moment I arrived, everything was exactly as described. The place was spotless, beautifully decorated, and had all the amenities I needed. The location was ideal — close to great restaurants, local attractions, and in a safe, quiet neighborhood. It made getting around very convenient. Susan was incredibly responsive, helpful, and genuinely welcoming. She provided excellent local recommendations and made sure I had everything I needed for a comfortable stay. I would 100% stay here again and recommend it to anyone looking for a clean, cozy, and relaxing place to getaway. Thank you for a wonderful stay!
Top guest favourite

Private room in Beacon
4.88 out of 5 average rating, 371 reviewsCalli's Room in Beacon 1794 Home Walk 2 Train
DawnRating, 5 stars3 days ago
This was my second time staying with Patricia and I love it! The house itself is beautiful. The walkability to restaurants, the waterfront and the train station is excellent. Patricia and Steve are so welcoming -- and it was really nice to have tea provided in the evening and a fresh brewed pot of coffee in the morning! I look forward to staying with them again!
Guest favourite

Private room in Beacon
4.93 out of 5 average rating, 122 reviewsPrivate Room With Private Entrance
AndriaRating, 5 stars4 months ago
Lots of thoughtful touches, like slippers, earplugs (definitely use them as it can get a little noisy with the sounds of the water heater), snacks, and Brita. The place has everything we needed for a weekend visiting Beacon/Cold Springs. Dan was very attentive and accommodating. Also had amazing pics and passages from his travels around the world! thanks for accommodating us, Dan!
Quick stats about holiday rentals in Wappinger
Total rentals
80 properties
Nightly prices starting at
$39 SGD 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
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- Hunter Mountain
- Fairfield Beach
- Rye Beach
- Mountain Creek Resort
- Rye Playland Beach
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Rye Town Beach
- Ringwood State Park
- Jennings Beach
- Seaside Beach
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Calf Pasture Beach
- Kent Falls State Park
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Sherwood Island State Park
- Van Cortlandt Park Golf Course
- Glen Island Beach