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Peekskill Holiday Rentals

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Holiday Rentals in Peekskill

Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (33)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is NZ$294
per night
27 May - 28 May
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
Cozy family-friendly home!
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
10.0 out of 10, Exceptional, (21)
"This is an attractive, well-laid out house with an extremely accommodating owner. The home is pretty small—great for two or three with very little play area inside for kids—but there are several great outside areas on the deck, around the pool and stream. In terms of accessibility, three steps up to the doorway, a step down to the master bedroom and a step up to the ensuite master bath."
Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
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View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (16)
"This house is located minutes from the highway making it easy to get to. Its a very scenic and country area so you feel farther away then you are. The house is extremely clean and well appointed it sits up high on a hill so you can enjoy the veiw of the country house across the street which has a small creek and gardens to enjoy theres even a pool to enjoy in summer months and a fire pit .this house was peaceful and perfect for the quick weekend getaway that we all needed. The host Pat was...
The price is NZ$463
per night
14 May - 15 May
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (1)
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is NZ$1,521
per night
13 May - 14 May
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (29)
"Our stay was wonderful! The house was super clean and just what we needed. The bed was comfortable and the game room even better for the little ones and adults :) thank you so much!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Property grounds
Lakefront New York Abode w/ Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (3)
"Clean, spacious, and many activities in a nice quiet town. The house comfortably fit our 10 people."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Fireplace
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (1)
"A very short but pleasant stay and the host gave us good communication."
The price is NZ$626
per night
20 May - 21 May
Contemporary Cozy Cottage
Outdoor spa tub
Lakefront/Legoland/Mt. Peter Retreat Under 1 Hour From NYC! Heated pool & Spa!
10.0 out of 10, Exceptional, (27)
"We had a lovely vacation at Ilya’s. Beautiful setting and so close to the city which was a huge plus!"
Lakefront/Legoland/Mt. Peter Retreat Under 1 Hour From NYC! Heated pool & Spa!
Fridge, microwave, oven, stovetop
Kick back & relax in this peaceful, stylish place to stay with the whole family.
10.0 out of 10, Exceptional, (11)
"Thank you, Malkita Homes, for a wonderful stay! The house was just as described - the perfect weekend retreat for a group of 15 adults."
Kick back & relax in this peaceful, stylish place to stay with the whole family.
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$440
per night
13 May - 14 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (39)
"Quiet, clean and very comfortable. Beautiful property located just minutes from town. Will definitely stay here again."
The price is NZ$359
per night
4 Jun - 5 Jun
Cozy country efficiency in the Hudson Valley
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
A heated pool
Hudson Valley Getaway: Heated Pool, Home Theater, Gym, Game Room, Bar, Fire Pit
9.4 out of 10, Exceptional, (9)
"I rented this property for my co-workers who were here for a retreat at my home in the area, and at the local community center. This home had everything we needed, and the host was easy to communicate with. We will definitely consider using this property again for future guests coming for work and family gatherings."
The price is NZ$1,330
per night
16 May - 17 May
Hudson Valley Getaway: Heated Pool, Home Theater, Gym, Game Room, Bar, Fire Pit
Fridge, microwave, oven, stovetop
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
9.4 out of 10, Exceptional, (10)
"Booked our stay over Ring Weekend at West Point. Quiet neighborhood, 15 minutes from Stoney Gate entrance to West Point. Wonderful well furnished clean and comfortable spot with 2 bedrooms. Friendly, prompt and kind communication during entire reservation and use process. Highly recommended!"
Beautiful Cozy 2 br in-law apt, prime Hudson Valley location
Exterior
Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking
9.2 out of 10, Wonderful, (13)
"Our family of 4 stayed here for a couple nights while visiting family. Super clean, well stocked, easy apartment! The owner was incredibly helpful and we couldn’t have asked for more! Looking forward to coming back!"
Stay on Main St! ~Walk to EVERYTHING West Point! Mountain Views/private parking
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Peekskill you may be interested in

Exterior
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley, an IHG Hotel
2.5 star property
9.2 out of 10, Wonderful, (954)
"Great customer service."
The price is NZ$281
per night
26 May - 27 May
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley, an IHG Hotel
Bar (on property)
The Abbey Inn & Spa
3.0 star property
9.2 out of 10, Wonderful, (101)
"This place is out a fairy tale beatiful clean great staff excellent food and wine outdoor garden gorgeous 😍 "
The price is NZ$825
per night
16 May - 17 May
The Abbey Inn & Spa
View from property
Inn on the Hudson
2.0 star property
6.8 out of 10, (1001)
"."
The price is NZ$207
per night
19 May - 20 May
Inn on the Hudson
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Peekskill holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Peekskill. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Peekskill. Seeing all the best attractions is bound to make you fall in love with Peekskill. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Peekskill short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Peekskill?

Yes, there are holiday rentals in Peekskill close to Lincoln Depot Museum, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront and mountain landscape in Peekskill. While you're here, grab a bite or have a drink at the restaurants.

How many holiday rentals are there in Peekskill?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Peekskill stay.

What’s there to see and do in Peekskill?

Enjoy the outdoors at Charles Point Pier Park and Peekskill Landing Park, or simply take in cultural attractions like Paramount Hudson Valley Theater and Peekskill Museum. Other places in town to visit include Blue Mountain Reservation and Depew Park.

What’s a holiday rental in Peekskill like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Peekskill. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family getaway.

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