
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

Private Hudson Valley Country Retreat
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

Summer Retreat! Amazing Pool, Playground, 7 acres!
This property is large and roomy with plenty beds to go around including the basement with the pool and ping pong tables plus a home gym with various equipments. The outdoors were fantastic with a very nice temperature controlled pool, Jacuzzi, swings set for the little ones and enough acreage to have a soccer match. The neighborhood was nice and quiet in a great country setting with lots of wildlife to enjoy to include lots of singing birds. Our family reunion was a great success due in part to the before mentioned surroundings. Douglas was always available to resolve minor issues, very responsive and accommodating, thanks for making our stay at this property a great one.

4Br Mountain Brook House on 130 acres w/ trails
Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Little owl Japanese teahouse: pool is OPEN
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.

Midcentury Modern ZenHouse Sculptor Studio
Very relaxing and peaceful stay at the Zenhouse for me, my husband and 3 month old boy. The guest house was relatively spacious and had all the amenities needed to relax with tea/coffee and grill food. Some of the fixtures in the guest house are a bit dated (e.g. bathroom, heater, etc.) but are all perfectly functional. The property is expansive with beautiful trees, streams and walkways throughout. Olga greeted us with a wonderful welcome including of the history of the property. We also enjoyed spotting the geese, chipmunks and other animals that roam around the grounds. We would come again when during warmer weather to enjoy the pool next time.

GOOD VIBEZ HOUSE! MiniGolf-Pool-HotTub-GameRm!
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!

Upstate Modern Scandinavian Barn in the Catskills
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Weekly house rentals

1956 House of the Year Award. Easy commute to NYC.
A unique architectural home built 1955 that’s set on 2 plus acres surrounded by mature hardwoods. Set in a lovely neighborhood. Lots of interesting Art and Literature available to enjoy.I had wanted to stay on several visits but this location wasn’t available. I lucked out for 3 nights and so glad I had the opportunity to. I will definitely book again. Gloria was a responsive host. Instructions were clear and detailed. Lots of closet space in the 3 bedrooms and plenty space, multiple sitting areas. Thank you Gloria.

Spacious, bright 5 bedroom house near West Point
I stayed here with my family and we absolutely loved it. It had everything we needed and more. We like to cook on our trips and the kitchen had everything we needed and more. Best stocked kitchenware I have ever found in all my travel. Host is thoughtful and proactive. Highly recommend

Architect's Hudson Valley Home in the Woods
We really enjoyed our stay at Olga’s! The design throughout the space is beautiful, and staying on the second floor feels like floating among the trees. It’s also wonderfully private, with great food spots nearby that make the location super convenient.

Dr. Ruth’s Serene Lake Retreat
After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.

Welcome to The Boathouse! Waterfront/Boats/Hot tub
we had a lovely time at Seth’s cottage by the river. Everything was very well appointed and comfortable. I think the beds were the best I’ve had an Airbnb. There was easy access to new Paltz and kingston. I have no hesitation in recommending Seth’s place.

Aster Place
Thanks. Quick comfy stay.

A nice place to getaway
We’ve stayed at Filiz’s place a few times and it’s perfect! Quiet, clean, and easy to get to where we needed to be. We’ll be back!

Waterfront Lake House
Absolutely beautiful stay, Brian is an amazing host and went above and beyond with instructions and helped whenever needed. Their place is located in such a beautiful area, it is quiet and within 10 min drive to stores. The space is very clean and organized. My guests and I felt right at home.
Private house rentals

Crystal Wave LakeHouse
Our family converged there for West Point graduation weekend. The home is easy to get to and about a 15 mile drive to Thayer gate . The weather was cold and damp so we all didn’t get to enjoy the outdoor space. My husband and son brought fishing rods and had a blast catch and release when we where there in the evenings.They took the provided kayaks for a spin and everyone else stayed warm indoors.The kitchen, dining area and living room in one big open space was nice so we could all be together. The bathrooms were spacious and clean.If I had known about this place sooner, I would have stayed a few times over football season. My dog sitter canceled on me last minute and the host was very accommodating for our dog. Highly recommend this property.

Camped Inn at Sundial Farm -- Tiny House
Hi! The house was cute and convenient for our purposes. We were on a tight schedule so could not be there when the utilities could be explained to us which put us at an extreme disadvantage. It's a cute place to get away. Thanks for your hospitality.

Bungalow near West Point on Hudson River
This was our second stay with Laura and it was wonderful again. The location is very convenient if you are traveling to West Point. The view from the backyard and sunroom is amazing. Yes, there is train noise but it didn't bother us. We will stay here again.

Summer Adventures in Cold Spring at Gilbo's
We were there for a USMA graduation, and the location / accommodations worked great. Handy having a decent grocery store two blocks away. The walking loop down to the Foundry and Cold Springs Park is delightful. Nice with our house guests (extended family and friends) to be able to spread out in the place. Kitchen was spacious and awesome for family meals. Pool wasn't open yet, but looked inviting to add to the outside BBQ area.

The Barger Wixon House
Stayed for West Point graduation. House was awesome. Hosts were more awsomelierist….. Highly recommend. GO ARMY! BEAT navy!

Accord River House
One of the cooler homes we’ve stayed in through Airbnb. Rob’s home was immaculate and well-appointed; the location couldn’t be better. We slept with the windows and doors open, utilizing the phantom screens, to listen to the gentle rolling falls outside. Incredible!

West Point Cottage
Highly recommend this place! It is absolutely perfect for any events at West Point. We were there for our daughter's graduation, and the location cannot be beat! It is also a very charming cottage with a great deck and yard, very clean and comfortable. Hosts were very helpful and responsive. Hope to stay there again!

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?!)
Quick stats about house rentals in Peekskill
Total rentals
20 properties
Nightly prices starting at
₹5,143 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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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Fairfield Beach
- Rye Beach
- Citi Field
- Mountain Creek Resort
- MetLife Stadium
- Yankee Stadium
- United Nations Headquarters
- Rye Playland Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Bronx Zoo
- Central Park Zoo
- Radio City Music Hall
- The Metropolitan Museum of Art
- Canarsie Beach
- Minnewaska State Park Preserve