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Peekskill Holiday Rentals

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Holiday Rentals in Peekskill

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

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
The price is NZ$710
includes taxes & fees
2 July - 3 July
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (15)
"Wonderful, comfortable home! Clean, user-friendly with great views!"
The price is NZ$1,451
includes taxes & fees
26 June - 27 June
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

The price is NZ$540
includes taxes & fees
24 June - 25 June
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Summer Castle: Pool, Game Room, BBQ - Pet Friendly

8.0 out of 10, Very good, (3)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is NZ$2,310
includes taxes & fees
21 July - 22 July
Summer Castle: Pool, Game Room, BBQ - Pet Friendly

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

8.6 out of 10, Excellent, (7)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is NZ$308
includes taxes & fees
24 June - 25 June
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (23)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is NZ$679
includes taxes & fees
24 June - 25 June
Contemporary Cozy Cottage

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is NZ$697
includes taxes & fees
24 June - 25 June
Rustic Cabin in Fishkill!

Chestnut on Willow Lake

8.0 out of 10, Very good, (1)
"We had a very nice stay!Chestnut on Willow Lake worked well for us!We loved the property and campfire on Friday evening! I wish we had had time to go over to the fire to enjoy it!"
The price is NZ$967
includes taxes & fees
24 June - 25 June
Chestnut on Willow Lake

Hickory on Willow Lake

8.0 out of 10, Very good, (1)
The price is NZ$1,028
includes taxes & fees
25 June - 26 June
Hickory on Willow Lake

Red Cottage - Lakeside Property!

The price is NZ$979
includes taxes & fees
24 June - 25 June
Red Cottage - Lakeside Property!

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

The price is NZ$387
includes taxes & fees
16 July - 17 July
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Gorgeous Garrison Gem Pool Sauna Hot Tub More

2.0 star property
Gorgeous Garrison Gem Pool Sauna Hot Tub More

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

9.8 out of 10, Exceptional, (18)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is NZ$559
includes taxes & fees
1 July - 2 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Updated, well equipped kitchen and comfortable living and sleeping spaces. We will definitely try to book here on our next visit to West Point. "
The price is NZ$1,386
includes taxes & fees
24 June - 25 June
West Point Family Retreat, 5 min walk to Thayer!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is NZ$575
includes taxes & fees
1 July - 2 July
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is NZ$637
includes taxes & fees
25 June - 26 June
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is NZ$1,839
includes taxes & fees
6 July - 7 July
Room for Everyone: Spacious 6BR West Point Retreat

Large, Cozy, Bright Business Class Corporate Retreat

9.0 out of 10, Wonderful, (13)
"It went well for us in a one night stay."
The price is NZ$1,142
includes taxes & fees
24 June - 25 June
Large, Cozy, Bright Business Class Corporate Retreat

Charming large Victorian in historic Newburgh

10.0 out of 10, Exceptional, (1)
The price is NZ$1,663
includes taxes & fees
26 June - 27 June
Charming large Victorian in historic Newburgh

Woodland Sanctuary - 6000ft retreat for pure relaxation!

The price is NZ$4,475
includes taxes & fees
28 June - 29 June
Woodland Sanctuary - 6000ft retreat for pure relaxation!
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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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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Peekskill offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself 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 Blue Mountain Reservation and Charles Point Pier 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.