Photo by Eugenio Ruiz

Holiday Rentals in Peekskill

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Peekskill

Charming 3-bedroom house with AC, WiFi in Peekskill

Charming 3-bedroom house with AC, WiFi in Peekskill

Global Luxury Suites White Plains

3.5 star property
7.0 out of 10, Good, (28)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is €239
includes taxes & fees
18 Feb - 19 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is €283
includes taxes & fees
18 Feb - 19 Feb
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

2.0 out of 10, (1)
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.6 out of 10, Exceptional, (9)
"Great property nice and cozy for a group of 6. Rooms and house were clean and very organized host provided coffee and bath basics. House was equipped with family games and kitchen and living room and deck all open floor plan. Working jacuzzi which was great after hitting the slopes and a lot of backyard space for kids to roam around. The host was communicative throughout the stay. Warwick town was 20 mins away and mount Peter was 15 mins away Woodbury commons are 20 mins away . Overall would...
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

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

10.0 out of 10, Exceptional, (75)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Historic 1800's Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800's Cornwall-On-Hudson Cottage!

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"
The price is €363
includes taxes & fees
18 Feb - 19 Feb
Contemporary Cozy Cottage

The Philip Johnson Wolfhouse

10.0 out of 10, Exceptional, (3)
"This house is an architectural gem with great views to the Hudson river and very close to Dia Beacon and really nice hikes. We were a group of 7 and really enjoyed our time together during our stay. Jeremy was really nice and accommodating. I highly recommend this house."
The Philip Johnson Wolfhouse

Kick back & relax in this peaceful, stylish place to stay with the whole family.

10.0 out of 10, Exceptional, (22)
"Our family went to the Hudson Valley area for a wedding. Pre stay communication with Malka was excellent and we all had a wonderful time. Lots of room for the kids to play and be entertained downstairs as well as upstairs in the Projection Room. The backyard was a great soccer area and the fire pit was great to sit around at night. Firewood on site was a real plus! I do recommend to anyone doing substantial cooking for many people to bring their own favorite pots and pans if possible though...
Kick back & relax in this peaceful, stylish place to stay with the whole family.

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.0 out of 10, Good, (15)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

10.0 out of 10, Exceptional, (55)
"This little attached apartment was the perfect size for me, and I felt very safe. I loved being at the top end of the cul de sac so it was quiet and there was an amazing view from the deck looking over and down the Hudson River. I had beautiful sunrises and the lights at night along the river were so pretty. The bedroom/living/dining room was perfect for one. The electric fireplace gave the room a cozy feel, the bed and couch were comfy, and there was plenty of hot water for showers and...
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (12)
"Property was better than advertised and exceeded all our expectations. All aspects of the VRBO process with the owner and management company were seamless. Highly recommend and will stay there again."
Bright Cornwall-On-Hudson Vacation Rental!

Charming 2-bedroom house with AC, WiFi in marvelous Nyack

2.0 star property
Charming 2-bedroom house with AC, WiFi in marvelous Nyack

Stay in the heart of Greenwood Lake minutes away from the lake

10.0 out of 10, Exceptional, (26)
"Fantastic little spot! Super cute and near everything! Absolutely enjoyed our stay and would stay again!"
Stay in the heart of Greenwood Lake minutes away from the lake

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (42)
"The perfect spot for a Beacon/Newburgh getaway! Great access to the towns, Storm King State Park, and Storm King Art Center! Lovely house, great game room (played so much ping pong and darts), and the hot tub was perfect."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Majestic RiverView Estate - Breathtaking Views

10.0 out of 10, Exceptional, (4)
"We booked a weekend away to celebrate family birthdays and were very happy to celebrate in such a special place. There was plenty of room for 11 of us (+ dog) and was a mix of modern touches and old world charm highlighting the legacy of the house. And the view of the Hudson was a highlight of our stay. Highly recommend!"
Majestic RiverView Estate - Breathtaking Views
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.
Don't see what you're looking for?
See all available properties in Peekskill
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Peekskill you may be interested in

Inn on the Hudson

2.0 star property
6.8 out of 10, (1002)
"Very quiet and cute"
The price is €97
includes taxes & fees
23 Feb - 24 Feb
Inn on the Hudson

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Having stayed here several times, we are consistently pleased with all that it has to offer!"
The price is €121
includes taxes & fees
16 Mar - 17 Mar
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

The Abbey Inn & Spa

4.0 star property
9.2 out of 10, Wonderful, (156)
"Nice spacious, clean room. But had no bath. Staff sent confusing messages changing appointments at spa and restaurant a few times due to weather they said. Main Elevator with carpet had strange smell. Otherwise hotel facility was nice. Have to walk to gym in basement of a nearby apartment building, which is a bit of an inconvenience. Nd front desk lady did not explain where gym was. So we walked around. Building inside trying to find it for a bit. There was no sign for it. View is nice...
The price is €370
includes taxes & fees
18 Feb - 19 Feb
The Abbey Inn & Spa
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.

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.

What are some of the best holiday rentals that Peekskill has to offer?

Charming 3-bedroom house with AC, WiFi in Peekskill: This highly rated holiday home rental in Peekskill offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and an oven. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Peekskill?

With 3 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 Depew Park and Blue Mountain Reservation, or simply take in cultural attractions like Paramount Hudson Valley Theater and Peekskill Museum. Other places in town to visit include Charles Point Pier Park and Dramatic Hall.

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.