A calm lake with a forested island in the distance, a picnic area, and a rocky shoreline.

Peekskill Holiday Rentals

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Our top choices for Peekskill holiday rentals

1. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is NZ$702
includes taxes & fees
16 Nov - 17 Nov
Contemporary Cozy Cottage

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is NZ$527
includes taxes & fees
15 Nov - 16 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

3. 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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is NZ$542
includes taxes & fees
16 Nov - 17 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

4. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is NZ$1,085
includes taxes & fees
16 Nov - 17 Nov
Spacious 4-bedroom house in northern Westchester with sweeping views

5. 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, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
The price is NZ$632
includes taxes & fees
18 Nov - 19 Nov
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

6. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is NZ$702
includes taxes & fees
13 Nov - 14 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

7. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Absolute comfortable stay. Everything you need and fantastic host!! Will be back."
United States
Lisa
The price is NZ$823
includes taxes & fees
15 Nov - 16 Nov
Walk-to-Lake Cottage With Grill for Peaceful Fall Days

8. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is NZ$725
includes taxes & fees
19 Nov - 20 Nov
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

9. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is NZ$730
includes taxes & fees
15 Nov - 16 Nov
Local Artist Inspired | Walk to WestPoint + King Bed

10. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is NZ$650
includes taxes & fees
8 Dec - 9 Dec
Fabulous 3bdrm Home w/parking!

11. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 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 NZ$354
includes taxes & fees
8 Dec - 9 Dec
Cozy 1-bedroom retreat minutes from West Point!

12. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
9.6 out of 10, Exceptional, (4 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is NZ$730
includes taxes & fees
15 Nov - 16 Nov
3BR Near West Point | Coffee Bar | Sleeps 6

13. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is NZ$590
includes taxes & fees
17 Nov - 18 Nov
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is NZ$633
includes taxes & fees
8 Dec - 9 Dec
Lovely 3BR Home with parking-Walk to WP Gate!

15. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
The price is NZ$588
includes taxes & fees
8 Dec - 9 Dec
Walk to WP Gate + Free Parking!

16. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is NZ$575
includes taxes & fees
16 Nov - 17 Nov
Perfect 2BR with Free Parking! Walk to West Point!

17. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
The price is NZ$1,161
includes taxes & fees
16 Nov - 17 Nov
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

18. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is NZ$599
includes taxes & fees
15 Nov - 16 Nov
Mountain-View 2BR Steps from Thayer Gate

19. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!
Highland Falls
The price is NZ$855
includes taxes & fees
8 Dec - 9 Dec
Hudson Valley/West Point Retreat w/ parking!

20. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is NZ$541
includes taxes & fees
15 Nov - 16 Nov
1BR Queen near NYC | Trails, Biking & Sauna Bliss
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

Find out more about Peekskill

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 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?

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 Hudson Valley Center for Contemporary Art 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.