Peekskill Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Peekskill holiday rentals

Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$689
HK$2,621 total
includes taxes & fees
18 May - 19 May
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (2 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
The price is HK$979
HK$2,130 total
includes taxes & fees
17 May - 18 May
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Such a cute place to stay"
United States
Melissa
The price is HK$1,175
HK$2,322 total
includes taxes & fees
16 May - 17 May
Cozy country efficiency in the Hudson Valley
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is HK$948
HK$1,649 total
includes taxes & fees
26 May - 27 May
Piermont Oasis
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,472
HK$2,488 total
includes taxes & fees
31 May - 1 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is HK$736
HK$2,210 total
includes taxes & fees
17 May - 18 May
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,057
HK$2,156 total
includes taxes & fees
16 May - 17 May
Charming 1-bedroom apartment in Carmel with WiFi, AC
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,424
HK$3,798 total
includes taxes & fees
17 May - 18 May
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (42 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
The price is HK$1,057
HK$2,313 total
includes taxes & fees
18 May - 19 May
Grant - A Tranquil One Bedroom Steps from River
TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,586
HK$3,086 total
includes taxes & fees
17 May - 18 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$962
HK$1,772 total
includes taxes & fees
27 May - 28 May
Cozy 1-bedroom retreat minutes from West Point!
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is HK$1,559
HK$1,867 total
includes taxes & fees
18 May - 19 May
Luxury home near West Point
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (50 reviews)
"We loved our stay. The room was so comfortable and had everything we needed. We loved being abl to walk to so many great restaurants and bars. "
United States
Amanda W.
The price is HK$940
HK$2,002 total
includes taxes & fees
20 May - 21 May
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (11 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is HK$1,191
HK$2,021 total
includes taxes & fees
17 May - 18 May
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$1,939
HK$2,550 total
includes taxes & fees
26 May - 27 May
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Lobby

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen

1 Queen Bed | ADA/RI Shower/Smoking/Kitchen
Fishkill
10.0 out of 10, Exceptional, (15 reviews)
"Good so far"
United States
Anonymous traveller
The price is HK$703
HK$795 total
includes taxes & fees
1 Jun - 2 Jun
1 Queen Bed | ADA/RI Shower/Smoking/Kitchen
Dining

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (91 reviews)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is HK$1,146
HK$2,474 total
includes taxes & fees
21 May - 22 May
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay. Cozy, warm, and clean! The host was also a good communicator and everything went smoothly."
United States
Samantha Esmé W.
The price is HK$901
HK$1,894 total
includes taxes & fees
18 May - 19 May
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is HK$1,566
HK$2,541 total
includes taxes & fees
3 Jun - 4 Jun
Luxury House Near West Point
Fridge, microwave, oven, stovetop

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
The price is HK$861
HK$2,642 total
includes taxes & fees
18 May - 19 May
Modern 1BR Apt / Free Parking / Near NYC
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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
"Easy check in, comfortable bed, minimal breakfast but enough to get us going."
William 1-night trip
Posted 4 hours ago
Spark by Hilton Fishkill

Find out more about Peekskill

Search for holiday rentals in Peekskill on Expedia! You can easily find your home rentals, villas, holiday apartments in Peekskill using one of the methods below:

  • View our selection of featured holiday rentals in Peekskill
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Look no further and take a look at our great range of rental properties in Peekskill!

Frequently asked questions

Can I find a holiday rental in Peekskill?

Yes, there are holiday rentals in Peekskill close to Paramount Hudson Valley Theater, 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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Peekskill is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

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

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.