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House vacation rentals in Wappinger

Find and book unique houses on Airbnb

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Popular amenities for Wappinger house rentals

House rentals with a pool

Guest favourite
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars7 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
Guest favourite
Home in Saugerties
4.94 out of 5 average rating, 70 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

JustinRating, 5 stars2 weeks ago
Highly recommend Sarah’s house. We stayed in the spring and it was beautiful. Spacious outdoor area with lots to do. There was plenty of space, lots of activities and stuff for our kids to play with; super family friendly. Also very close to all the towns we wanted to visiting and natural attractions up in Hudson River valley. We would stay again thank you !
Top guest favourite
Home in Warwick
4.98 out of 5 average rating, 61 reviews

4 bedroom house with pool (Kids & Dog Friendly)

MichelleRating, 5 stars1 week ago
Betty was so quick to help when our original location to stay was cancelled. I am so thankful her property was available and how easy she made the process after what we went through!
Guest favourite
Home in Newburgh
4.83 out of 5 average rating, 82 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars2 weeks ago
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.
Guest favourite
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Superhost
Home in Stanfordville
5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.
Guest favourite
Home in Woodstock
4.86 out of 5 average rating, 132 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

HelaRating, 5 stars1 month ago
Beautiful home with amazing views. The house was very clean and spacious, the views were amazing. Susanna was very responsive and gave clear instructions. We had a very relaxing weekend and enjoyed very much staying at the house. We would love to come back.
Guest favourite
Home in West Milford
4.98 out of 5 average rating, 150 reviews

On The Rocks In The Hot Tub

RicardoRating, 5 stars1 week ago
I had an absolutely wonderful stay at Marcela's Airbnb! I was in town for the Spartan Race and needed a comfortable place to relax after the event, and Marcela's place was the perfect spot. The house is spacious and inviting, offering plenty of room to unwind. After pushing myself during the race, the hot tub was an absolute dream—perfectly maintained, spacious, and the ideal place to soak in and let the stress melt away. Marcela herself was incredibly polite, responsive, and thoughtful, making sure I had everything I needed for a relaxing stay. She really went out of her way to ensure I was comfortable. If you're looking for a peaceful and rejuvenating retreat, especially after a big event, I highly recommend Marcela's place!

Weekly house rentals

Guest favourite
Home in Mount Tremper
4.9 out of 5 average rating, 224 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Tracy,JRating, 5 stars1 month ago
A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.
Superhost
Home in Smallwood
4.79 out of 5 average rating, 162 reviews

Cozy Catskill Lake Community Home

PeterRating, 5 stars26 months ago
We had a lovely and relaxing weekend at John’s place. Thanks for the great local tips.
Guest favourite
Home in Gardiner
4.91 out of 5 average rating, 248 reviews

Riverfront Stone Cottage Private/ hot tub/ boats

BrandiRating, 5 stars1 week ago
This house was spectacular. Seth was great about getting back to me with any questions. We all found the property to be peaceful and relaxing. The kitchen had a lot of spices that were helpful, but be sure to bring along food storage items of your own. Every room had beautiful earthy details and the charm was endless. The amenities were incredible and the back yard view was perfect. Will absolutely be back for another stay!
Superhost
Home in Wallkill
4.86 out of 5 average rating, 121 reviews

Modern Upstate Gem Surrounded by Trees | Hot Tub

RobertoRating, 5 stars1 month ago
I had a wonderful stay at this beautiful modern home in Wallkill, NY. Tucked away on a quiet street with plenty of privacy from the surrounding trees, it felt like the perfect escape from the city. My favorite part was the open-concept kitchen and living area, with expansive windows that made it feel like I was immersed in nature while still enjoying the comfort of being indoors. It was the ideal space to rest, relax, and recharge. If you're looking for a peaceful getaway, I highly recommend this home!
Guest favourite
Home in Garrison
4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars1 month ago
Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!
Superhost
Home in Ancram
4.8 out of 5 average rating, 112 reviews

Secluded Post-And-Beam Retreat

SarahRating, 5 stars2 months ago
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.
Guest favourite
Home in Mount Tremper
4.97 out of 5 average rating, 155 reviews

Perfect Abbey Road Retreat

MeganRating, 5 stars4 months ago
What a beautiful place to spend Christmas!! Before moving to Australia next year we wanted one more cold snowy holiday. While we didn’t have as much snow as we’d hoped, it was still an amazing stay. The house is so homey and comfortable. With two young neurodivergent kids it’s hard being in a new place and the kids room was absolutely essential to our time there. The mattress in the primary bedroom is heavenly, and the overall decor and vibe of the house were incredible with enough room for everyone to have their own space (MIL included!). The kitchen was perfectly stocked and felt like we were right at home. We made a day trip out to Hunter Mountain to go tubing and a trip down to Kingston to Aldi and Target as well. Noah and Brandon were absolutely amazing hosts, Noah was extremely responsive even before we booked, and made sure we had what we need as our trip got closer. I would absolutely make the trip again and am so thankful for the memories we made!
Top guest favourite
Home in Halcott
4.98 out of 5 average rating, 102 reviews

Modern Mountain Retreat with Views on 18 Acres

PolinaRating, 5 stars2 weeks ago
We have been to the Catskills numerous times but our stay here outshined all the rest. The home was amazing, the bathrooms were stunning and the location was very private. Clearly Paul and Michael put a lot of time and effort into decorating and making the place feel like home. There was also a guide with recommended restaurants, hikes, nearby farms, and things to do that was so helpful. We would 100% come back just to stay here again.

Private house rentals

Top guest favourite
Home in High Falls
5 out of 5 average rating, 227 reviews

Our Place - A Big Little House

DoraRating, 5 stars2 months ago
Excellent place to stay at. Truly luxurious with modern fixtures and appliances. Very clean and neat with tasteful decor. Great view in the winter, extremely peaceful and private. Driveway definitely requires AWD due to ice and snow in the winter. Tons of towels and toiletries provided. Patti and Bob were so helpful and courteous. Many great suggestions for places to eat and things to do. Very knowledgeable on the local trails. Wouldn't hesitate to return!
Superhost
Home in Fleischmanns
4.91 out of 5 average rating, 78 reviews

Secluded Open Air Cabin

AsshurRating, 5 stars2 months ago
This Airbnb is completely amazing. It is beautiful. It is spacious. It is great for a group. It comes fully stocked with most of the basic things you need like a fully functional kitchen with things like syrup and jam and all of that in there. The host was completely responsive. If you are planning to go to ski, it is close to the mountain. I completely enjoyed our stay.
Superhost
Home in Windham
4.73 out of 5 average rating, 30 reviews

Beautiful, cozy and private house

AnushkaRating, 5 stars1 week ago
We loved our stay here!! It is very accessible to a lot of hikes in upstate. The place was super clean. You would find most amenities in the house for your stay. Loved it.
Guest favourite
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries
Guest favourite
Home in West Milford
4.91 out of 5 average rating, 143 reviews

Large family house on the lake

MuhammadRating, 5 stars4 months ago
Jose was a great host—very responsive and proactive. It snowed the day we arrived, and Jose made sure the snow was cleared so we could fully enjoy the place. I will definitely be looking forward to coming back.
Superhost
Home in Ulster Park
4.88 out of 5 average rating, 228 reviews

Entire lake house to yourself. Great for groups

Maggie FuentesRating, 5 stars2 weeks ago
Scott is amazing! The airbnb was incredible! Lovely placed filled for immense and loving memories. He allowed me a late Check-Out which was wonderful. Definitely recommend you guys coming more often!
Superhost
Home in Margaretville
4.83 out of 5 average rating, 96 reviews

FOUR SEASON Huge Catskills Home-Secret Waterfall

PaulRating, 5 stars2 months ago
We had a lovely time at the house. Great amenities and location!
Top guest favourite
Home in Craryville
4.92 out of 5 average rating, 113 reviews

The Gatehouse at Raspberry Ridge

JenniferRating, 5 stars2 weeks ago
If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.

Quick stats about house rentals in Wappinger

  • Total rentals

    30 properties

  • Nightly prices starting at

    $55 CAD before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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