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Peekskill Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Peekskill vacation rentals

Coffee/tea maker, fridge, oven, stovetop

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.6 out of 10, Exceptional, (23 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is ￥18,843
￥50,281 total
includes taxes & fees
Jul 25 - Jul 26
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥20,388
￥65,249 total
includes taxes & fees
Jul 26 - Jul 27
House on the Babbling Brook- Quiet 2BR + King Bed!
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, (140 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥32,294
￥53,946 total
includes taxes & fees
Aug 10 - Aug 11
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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, (3 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 ￥25,517
￥44,308 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 1-bedroom retreat minutes from West Point!
Coffee/tea maker, fridge, microwave, oven

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is ￥36,866
￥69,153 total
includes taxes & fees
Aug 4 - Aug 5
Contemporary Cozy Cottage
3 bedrooms, desk, iron/ironing board, travel crib

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (18 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is ￥24,086
￥74,501 total
includes taxes & fees
Jul 29 - Jul 30
Local Artist Inspired | Walk to WestPoint + King Bed
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 ￥30,869
￥84,689 total
includes taxes & fees
Jul 27 - Jul 28
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very Good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥26,052
￥83,413 total
includes taxes & fees
Jul 26 - Jul 27
3BR West Point Retreat-3min to Back Gate+ King Bed
Coffee/tea maker, fridge, microwave, oven

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 ￥35,450
￥58,905 total
includes taxes & fees
Jul 29 - Jul 30
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is ￥35,450
￥58,905 total
includes taxes & fees
Jul 29 - Jul 30
Walk to WP Gate + Free Parking!
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, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is ￥42,863
￥75,886 total
includes taxes & fees
Aug 22 - Aug 23
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Interior

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 ￥37,162
￥66,726 total
includes taxes & fees
Jul 27 - Jul 28
Lovely 3BR Home with parking-Walk to WP Gate!
Property grounds

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

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Newburgh
10.0 out of 10, Exceptional, (72 reviews)
"Great place for a few days R & R. Definately recommended"
United States
Mary R.
The price is ￥14,599
￥35,634 total
includes taxes & fees
Jul 27 - Jul 28
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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, (46 reviews)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
The price is ￥22,019
￥46,681 total
includes taxes & fees
Aug 17 - Aug 18
Grant - A Tranquil One Bedroom Steps from River
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ￥56,685
￥90,029 total
includes taxes & fees
Aug 4 - Aug 5
Fabulous 3bdrm Home w/parking!
1 bedroom, WiFi (free)

2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is ￥17,940
￥20,294 total
includes taxes & fees
Jul 29 - Jul 30
2 Queen Beds | Non-Smoking, Kitchen
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥37,030
￥43,051 total
includes taxes & fees
Jul 26 - Jul 27
Harriman Outdoor Center - Mountain Laurel Cabin
Outdoor spa tub

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (10 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is ￥36,211
￥71,807 total
includes taxes & fees
Jul 29 - Jul 30
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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, (12 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 ￥17,204
￥32,437 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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 ￥23,922
￥38,506 total
includes taxes & fees
Aug 19 - Aug 20
Piermont Oasis
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

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Great place"
Virginia 6-night trip
Posted 7 hours ago
DoubleTree by Hilton Hotel Nanuet

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
  • Use the map to find apartments and other holiday homes in the Peekskill neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Peekskill while they last

Look no further and take a look at our great range of rental properties in Peekskill!

Frequently asked questions

Can I find a vacation rental in Peekskill?

Yes, there are vacation rentals in Peekskill close to Paramount Hudson Valley Theater, or you can go with a more remote option if you're looking for extra privacy while you relax. 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 vacation rentals that Peekskill has to offer?

🤣🏡 "Welcome to our basement suite, where humor and professionalism coexist!: This Peekskill vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals are there in Peekskill?

With 3 Expedia vacation rentals, you're sure 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 vacation rental in Peekskill like?

Vacation rentals are privately owned properties you can book for a long or short time in Peekskill. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.