
House vacation rentals in Peekskill
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Top-rated house rentals in Peekskill
Guests agree: these houses are highly rated for location, cleanliness, and more.
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Popular amenities for Peekskill house rentals
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.

4 bedroom house with pool (Kids & Dog Friendly)
Bettys home was a wonderful place for our 7 family members to stay. It was very comfortable and well equipped, with thoughtful amenities and lots of room. The fenced in yard was great for our dog, and the neighborhood quiet and close to the lovely towns of Warwick and Sugar Loaf. Betty was extremely responsive and kind enough to let us check in a few hours early. We would definitely stay here again!!

Entire Home (private pool), Event Friendly
I had a wonderful stay at this Airbnb! The space was clean, comfortable, and had all the amenities I needed. The host was friendly and very responsive, making check-in and check-out easy. The location was also perfect. Highly recommend this place!

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.

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
What an absolutely fantastic property! The home was perfect for our party of eight adults for a 50th birthday. Woodstock is the most adorable town with tons of fun things to do. You must get the stuffed bagels from moonrise. We couldn’t have expected a better experience with the house, the amenities, and The kitchen was very well appointed. I would absolutely come back here again and probably will.

Beautiful Lakefront Retreat with Private Dock
We enjoyed our stay and loved the views of the lake from the living room and porch. We had everything we needed for a nice family vacation. We would definitely stay again!

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

Sunset on the lake front/Kayak Permit#34323
The walk from the street to the entrance door could be challenging for someone with physical limitations, and the room air conditioners were a little loud, but everything else was wonderful. The outside of the house does not represent the beautifully remodeled interior. Kitchen had all modern necessary appliances, cookware, utensils and dinnerware. Bathrooms were stocked with towels, shampoo, conditioner, body wash, hair dryers etc. Modern washer/dryer in the basement. Great sunrises and lake view from the front deck. Children enjoyed fishing from the dock and sharing the 2 provided double kayaks. 10-15 minute drive to public beach, boat rentals, dining and groceries. 30 minute drive to Legoland.

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
Beautiful home and nice getaway from the city! Highly recommend this property for anyone looking for a relaxing weekend, beautiful views and amazing home. Thank you for a wonderful stay! We look forward to coming back!

Entire lake house to yourself. Great for groups
Scott's place was great. We were so relaxed and felt right at home. We will be going back which is the best compliment I can give an AirBnB. The views were beautiful!

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.
Private house rentals

Our Place - A Big Little House
This was our 3rd time staying at Patti's -- and we will back for a 4th! Which at first sounded crazy to us. My girlfriend and I enjoy traveling and finding new places is always fun but this air bnb is worth the repeat returns! Patti does so much to make sure it's a special stay by curating a beautiful home with thoughtful touches. It's become a tradition to visit this place and enjoy nature, the hot tub plus all the nearby small towns. Looking forward until the next time.

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

Secluded Oasis w/ Fire Place In Stone Ridge
Jane and Klay were great hosts and their home in Stone Ridge was beautiful and spacious with great amenities. We loved the fireplace and our dog loved the huge front and backyard with easy to access trails right from the property. The hosts were proactive with communication and gave really nice recommendations for local hikes and restaurants. We had a beautiful snowy weekend and would definitely love to come back. Thanks again!!

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.

Charming Retreat 3B/3B Garrison, 2 Fireplaces
There were 5 of us, with another 6 staying in another nearby air bnb. We had Thanksgiving in our house and found everything we needed to cook. Seating was a bit challenging, but we made it work and it was very comfortable. The location is in the woods with lots of boulders and rocks, which we all loved. We found the place easily using GPS. Everyone’s bed was comfy. Close enough to what we wanted, just far enough away to make it an adventure. Because it was so cold and grey, we didn’t hike, but saw plenty of opportunities (maybe next time?!)

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.

Home Sweet Hudson: A Retreat - Pond House
Amazing cabin in a remote location with all necessary amenities far away from the city. Our best AirBnB experience so far and would love to go back
Quick stats about house rentals in Peekskill
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
910 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
- Yankee Stadium
- Citi Field
- Inwood Hill Park
- MetLife Stadium
- Bronx Zoo
- Astoria Park
- Rockefeller Center
- United Nations Headquarters
- Statue of Liberty
- Kings Theatre