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Search Vacation Homes in Peekskill

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Oct 3 - Oct 5

Vacation Homes in Peekskill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (26)
"Perfect for small family stay over for a wedding ! "
$296 nightly
The price is $335
Aug 31 - Sep 1
Total includes taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Serene Hudson Valley Escape w/ Pool & Grill
Fridge, microwave, stovetop, dishwasher

Serene Hudson Valley Escape w/ Pool & Grill

10.0 out of 10, Exceptional, (1)
"An amazing stay in the 4th of July weekend- great place, double pool, giant rooms and everything in, included a patio for chillout, grilling and enjoy weekends with family and friends. Also, owners are nice, really kind and we definitely stay in touch for future escapes"
Serene Hudson Valley Escape w/ Pool & Grill
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Relax in a hot tub with a serene lake and forest view.

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (17)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
$512 nightly
The price is $579
Aug 6 - Aug 7
Total includes taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (35)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (85)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Microwave, oven, stovetop, dishwasher

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.
Modern NY Home w/ Views By Hudson Valley Hiking!
Relax in this stylish living space with a large sofa, matching ottoman, and modern light fixture.

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
The Woodbury Cottage
Relax in a serene outdoor space surrounded by lush greenery and trees, perfect for unwinding with a hammock and golf course nearby.

The Woodbury Cottage

8.8 out of 10, Excellent, (23)
"Really enjoyed our stay at this comfy cottage. Easily slept a family of 3 with plenty of room to lounge around. It's an older cottage, but the owner has added a lot of neat touches that make this a nice place to stay in this area."
The Woodbury Cottage
Charming Highland Falls Home < 2 Mi to West Point!
Cozy cottage with a covered porch, gabled roof, and a charming garden.

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Prepare meals in the spacious kitchen with a large island and appliances.

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (36)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Cozy living space with a fireplace, comfortable seating, and a dining area.

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.2 out of 10, Wonderful, (7)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Cozy Cabin with Sauna & Firepit!
Enjoy a peaceful retreat on this serene property with a covered patio, perfect for relaxing with a seating area and umbrella.

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (34)
"We enjoyed our short stay at this comfy little cabin! It’s cozy and has a “lived-in” feel—definitely a bit worn, but still charming and functional. The outdoor space is the real highlight: the deck, fire pit, and sauna were perfect for relaxing. It’s also in a great location near wineries and some beautiful hikes.Just a heads-up: the cabin is at the end of a pretty rough dirt road, so be prepared for a bumpy ride in. It feels nicely tucked away, but it’s not completely isolated—there are...
Cozy Cabin with Sauna & Firepit!
Hickory on Willow Lake
Escape to a serene oasis beneath a triangular gazebo, surrounded by lush greenery and a tranquil hillside setting.

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
$536 nightly
The price is $610
Aug 6 - Aug 7
Total includes taxes and fees
Hickory on Willow Lake
Contemporary Cozy Cottage
Cozy retreat with a natural touch, featuring a large artificial tree and potted plants.

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (26)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
$367 nightly
The price is $420
Aug 6 - Aug 7
Total includes taxes and fees
Contemporary Cozy Cottage
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Kitchen features microwave, toaster, and oven, along with a large sink and staircase to the upper level.

Home: 2 Mi to Thayer Gate at U.S. Military Academy

10.0 out of 10, Exceptional, (2)
"Your home was amazing! My family and I enjoyed every minute! "
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Aspen In Airmont NY
Enjoy cooking in this well-equipped kitchen with a range, oven, and island with sink and oven.

Aspen In Airmont NY

10.0 out of 10, Exceptional, (6)
"We had an excellent stay in this beautiful house. Favorite thing is the magnificent dining table."
Aspen In Airmont NY
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Enjoy cooking in this kitchen with sleek appliances, light grey cabinetry, and a wooden floor.

Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town

10.0 out of 10, Exceptional, (3)
"The house was big enough for 2 families. It was very clean and comfortable. The property is beautiful and Cold Springs was the perfect spot for everything we wanted to do while in NY. The caretakers were very responsive and accommodating. We would definitely stay here again. "
Spacious 5-bedroom house in the woods in Cold Spring just 5 minutes from town
Lake Carmel Access: Waterfront Home w/ Deck!
Enjoy cooking in this well-equipped kitchen with a double sink, microwave, stove, and dishwasher.

Lake Carmel Access: Waterfront Home w/ Deck!

10.0 out of 10, Exceptional, (1)
"Love the home wonderful location. The view is breathtaking. The owner responded timely to any request. "
Lake Carmel Access: Waterfront Home w/ Deck!
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
Cozy retreat with a desk, lamp, and vase with flowers.

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (39)
"Everything was good. Heather was very attentive."
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
Chestnut on Willow Lake
Enjoy cooking in this well-equipped kitchen with a stove, sink, and refrigerator.

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
$508 nightly
The price is $578
Aug 6 - Aug 7
Total includes taxes and fees
Chestnut on Willow Lake
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.
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Top Peekskill Hotel Reviews

Marriott Park Ridge

Marriott Park Ridge

10/10 Excellent
"Everything was Great but Breakfast should be included "
Schrod 2-night trip
Posted 1 day ago
Marriott Park Ridge