House holiday rentals in Peekskill

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Popular amenities for Peekskill house rentals

House rentals with a pool

Top Guest favourite
Home in New Paltz
4.98 out of 5 average rating, 489 reviews

midcentury mod * POOL * walk out trail to mohonk

EleonoraRating, 5 stars2 weeks ago
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍
Guest favourite
Home in Warwick
4.93 out of 5 average rating, 108 reviews

Summer Retreat! Amazing Pool, Playground, 7 acres!

JohanyRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 143 reviews

4Br Mountain Brook House on 130 acres w/ trails

DanielaRating, 5 stars3 weeks ago
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!
Superhost
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Woodstock
4.92 out of 5 average rating, 244 reviews

Little owl Japanese teahouse: pool is OPEN

JaneRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars5 days ago
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.
Guest favourite
Home in Commack
4.99 out of 5 average rating, 139 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

AliceRating, 5 stars3 weeks ago
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!
Top Guest favourite
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars3 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.

Weekly house rentals

Guest favourite
Home in Putnam Valley
4.96 out of 5 average rating, 84 reviews

Crystal Wave LakeHouse

SheriRating, 5 stars3 weeks ago
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.
Superhost
Home in Philipstown
4.73 out of 5 average rating, 150 reviews

Bungalow near West Point on Hudson River

AmyRating, 5 stars4 weeks ago
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.
Guest favourite
Home in Cold Spring
4.91 out of 5 average rating, 55 reviews

Summer Adventures in Cold Spring at Gilbo's

BillRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Putnam Valley
5 out of 5 average rating, 10 reviews

Dr. Ruth’s Serene Lake Retreat

EvanRating, 5 stars5 months ago
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.
Guest favourite
Home in Fort Montgomery
4.92 out of 5 average rating, 37 reviews

West Point Cottage

SamanthaRating, 5 stars2 weeks ago
My partner and I booked Philomena and Derek’s place for Memorial Day wknd to attend a wedding at West Point. It was the perfect location and a cute space. We went to dinner at a restaurant nearby called the Bird and Bottle Inn which was also great.
Top Guest favourite
Home in Cold Spring
5 out of 5 average rating, 35 reviews

Home in Cold Spring- Farm Stay!

BeckyRating, 5 stars4 weeks ago
Beautiful home, designed and decorated with such thoughtfulness. Cheryl&Jamie were very generous, providing us with farm fresh eggs, snacks and carrots for the animals. The house was fully equipped with games, kitchen supplies, towels etc. Drivable to many towns. We are already planning for our next trip here.
Top Guest favourite
Home in Mohegan Lake
4.95 out of 5 average rating, 57 reviews

A nice place to getaway

LizRating, 5 stars1 month ago
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!
Guest favourite
Home in Putnam Valley
4.97 out of 5 average rating, 66 reviews

Waterfront Lake House

KayleeRating, 5 stars1 week ago
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

Top Guest favourite
Home in Philipstown
5 out of 5 average rating, 23 reviews

Tranquil Hudson Valley Retreat with Cedar Hot Tub

ZiweiRating, 5 stars2 days ago
Great place to stay for a family trip. Beautiful surroundings and a great modern touch up kitchen.
Top Guest favourite
Home in Cold Spring
4.89 out of 5 average rating, 46 reviews

Cabin with a View

TerriRating, 5 stars2 months ago
Ellen’s place was beautiful and cozy. The kitchen worked perfectly and even though it was April it was still a bit chilly so the wood stove was a welcome amenity. The shower was great and there was a soaking tub. It was quiet and beautiful. We like all the art and it was very homey.
Guest favourite
Home in Putnam Valley
4.94 out of 5 average rating, 68 reviews

Chic Cozy Upstate Cabin Just 1 Hr From NYC!

AndrewRating, 5 stars1 month ago
Our second time visiting and had a wonderful stay! The house is lovely with a lot of space, a great kitchen, we used the Nespresso machine for great coffee, the grill (6 burner!) was great for cooking a lot, and the house has some outdoor space out back which was great for the kids. You can also use the finished basement for toddler play! The upstairs (sort of a loft) is great for relaxing on a couch and watching TV or running on a treadmill. The stairs going up have gaps so you may want to bring a baby gate for those (wide stair entrance). The house had most spices we would want and oils, so it was so easy, and the fridge is lovely to use! There's filtered instant hot water which is so nice for cooking and for tea! As you can tell, we love this place.
Guest favourite
Home in Ossining
4.89 out of 5 average rating, 35 reviews

Hudson Valley Escape

KellyRating, 5 stars1 month ago
Staying at this stunning Victorian home in Ossining was an absolute dream. From the moment we walked in, we felt completely at home. The house is full of warmth and character, with so many cozy sitting rooms to choose from — each one with its own unique charm. Every detail of the décor felt thoughtfully chosen, striking a perfect balance between historic charm and comfort. We especially loved relaxing on the back porch, taking in the beautiful view of the Hudson River. Jeff was a fantastic host — so friendly, easy to communicate with, and full of great local tips. His guidebook made exploring the area so much easier, and really helped us make the most of our stay. We couldn’t have asked for a better place or a better host. Highly recommend if you're looking for a special getaway with true character!
Top Guest favourite
Home in Philipstown
5 out of 5 average rating, 26 reviews

Charming Retreat 3B/3B Garrison, 2 Fireplaces

BibiRating, 5 stars6 months ago
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?!)
Top Guest favourite
Home in Narrowsburg
4.94 out of 5 average rating, 51 reviews

Modern Secluded Retreat

GajaRating, 5 stars3 weeks ago
Beautiful, private, and quiet spot to enjoy a night away. Lovely modern decor, birds chirping, and very comfy bed! We had a great time
Guest favourite
Home in Cold Spring
5 out of 5 average rating, 9 reviews

Cold Spring Cottage

TraceyRating, 5 stars3 weeks ago
Al's home is amazing. We were I'm the area for graduation at West Point. Our entire family was able to stay together, share meals, and celebrate our graduate. The house is impeccable, updated, and beautiful. We all commented on how every detail was well done. Al was very responsive and sent more towels when needed. I could not have asked for an overall better experience for my family.
Top Guest favourite
Home in Philipstown
5 out of 5 average rating, 14 reviews

Charming contemporary cottage with lap pool

MikeRating, 5 stars3 weeks ago
Jad was an amazing host. Super responsive and always aiming to make us comfortable and make sure our needs or requests were addressed. Clearly, he's put a lot of work into this unique property. It housed our extended family of 8 well. He was super flexible about checking in as we arrived earlier and the property was ready. This made for a much less hectic day on our first day. Highly recommend this cottage. He even had the pool ready for our use, but the unseasonably cold weather prevented us from enjoying the pool. Thanks for being so responsive.

Quick stats about house rentals in Peekskill

  • Total rentals

    20 properties

  • Nightly prices starting at

    $99 NZD 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

  • Wi-Fi availability

    20 properties include access to Wi-Fi

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