
House holiday rentals in Peekskill
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Top-rated house rentals in Peekskill
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Popular amenities for house rentals in Peekskill
House rentals with a pool

Perfect Family Retreat•Pool•Volleyball•Firepit
We stayed as a family of 4, including a 1 year old and 3.5 year old. The place was extremely comfortable and had everything we would need for our stay. The kids enjoyed the playroom and kids room with lot of toys and books. Kitchen was fully stocked with plates, utensils, cooking ware, and a high chair. Place could easily accommodate more people, very clean, comfy beds. Property manager was very responsive. Short drive to downtown area. Lastly, great outdoor area, we’d love to plan a trip there when warmer as well!

Great Family Times in this 5 Bedroom House
My family and I had a beautiful stay and I couldn’t have asked for a better rental. The Airbnb was huge with more than enough room for everyone and the backyard was large and spacious enough to have everyone eat comfortably. If I ever need another large rental you can bet I’m gonna check here first.

Entire Home (private pool), Event Friendly
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.

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

The Round House w/ Heated Pool
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.

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

Entire House Hot tub Barrel Sauna Private Backyard
I have been to many places but this house was top notch I'm glad I got to stay there with my family. everyone was very happy with the property. I would like to stay in the summer as well

On The Rocks In The Hot Tub
Great place. loved the pool table, darts and shall shuffleboard. lots of good wineries and cider places within 25 mins. pennings is our fav. didn't use the hot tub so couldn't comment but looked nice and private. driveway is steep but easily driveable. recommended. also didn't have coffee filters and they paid for some to be delivered same day! sweet.
Weekly house rentals

Stunning Modern Barn minutes from Woodstock 21N195
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.

Cozy Catskill Lake Community Home
We had a lovely and relaxing weekend at John’s place. Thanks for the great local tips.

Riverfront Stone Cottage Private/ hot tub/ boats
Excellent stay! Our group had a great time, lots of nearby hiking and excellent restaurants.

Modern Upstate Gem Surrounded by Trees | Hot Tub
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!

Hudson Valley Mountaintop Riverview
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!

Home away from home
The house was as advertised with plenty of space for our weekend men's retreat group of 7. We made use of the fire pit out back and the grill. Patricia was very helpful to provide us with several nearby hiking trail options. A good value for the money spent.

Secluded Post-And-Beam Retreat
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.

Perfect Abbey Road Retreat
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!
Private house rentals

Mahali Petu - A Big Little House
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!

Secluded Open Air Cabin
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.

Serene Country home 24 mi Mohawk ski area
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

Large family house on the lake
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.

Entire lake house to yourself. Great for groups
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!

FOUR SEASON Huge Catskills Home-Secret Waterfall
We had a lovely time at the house. Great amenities and location!

The Gatehouse at Raspberry Ridge
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.

Comfortable Entire House for rent. 4 bed, 3 baths
This was our second stay at Robert’s place and once again we really enjoyed staying at his house. Robert is a very friendly and responsive host and the house is great. Would definitely stay there again.
Quick stats about house rentals in Peekskill
Total rentals
20 properties
Nightly prices starting at
£45 before taxes and fees
Total number of reviews
880 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Tenement Museum
- Riverside Park
- Mountain Creek Resort
- Comedy Cellar
- Apollo Theater
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- Inwood Hill Park
- MetLife Stadium
- United Nations Headquarters
- Bronx Zoo
- Astoria Park
- Rockefeller Center
- Statue of Liberty
- Minnewaska State Park Preserve