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

Peekskill Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Peekskill holiday rentals

TV

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

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
9.0 out of 10, Wonderful, (4 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$1,153
HK$2,056 total
includes taxes & fees
15 Sept - 16 Sept
Cozy 1-bedroom retreat minutes from West Point!
Property grounds

2. 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, (144 reviews)
"We had a great stay!!"
United States
Jasmine
The price is HK$1,553
HK$2,593 total
includes taxes & fees
23 Sept - 24 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Terrace/patio

3. 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, (11 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$980
HK$3,137 total
includes taxes & fees
14 Sept - 15 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!
Desk, free WiFi, bed sheets

4. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2 reviews)
"Great stay!"
United States
Ann S.
The price is HK$1,214
HK$2,438 total
includes taxes & fees
17 Sept - 18 Sept
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
3 bedrooms, desk, iron/ironing board, free WiFi

5. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.4 out of 10, Exceptional, (8 reviews)
"Great location and super host. "
United States
James U.
The price is HK$1,474
HK$3,980 total
includes taxes & fees
7 Oct - 8 Oct
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Interior

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

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"We had a great stay at Joseph’s home. The property was very clean, spacious, and well prepared for guests. My work team and I felt comfortable right away, and the house had everything we needed for both a productive and relaxing stay.Joseph was always kind, professional, and quick to respond, which made a big difference. I would recommend this property without hesitation."
United States
ROHID S.
The price is HK$1,019
HK$3,441 total
includes taxes & fees
15 Sept - 16 Sept
3BR Near West Point | Coffee Bar | Sleeps 6
Coffee/tea maker, fridge, microwave, oven

7. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (40 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 HK$1,961
HK$3,543 total
includes taxes & fees
3 Oct - 4 Oct
Contemporary Cozy Cottage
Property grounds

8. 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 HK$1,090
HK$3,673 total
includes taxes & fees
16 Sept - 17 Sept
3BR West Point Retreat-3min to Back Gate+ King Bed
Coffee/tea maker, fridge, microwave, oven

9. 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 HK$2,017
HK$3,262 total
includes taxes & fees
15 Sept - 16 Sept
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Outdoor dining

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

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
10.0 out of 10, Exceptional, (1 review)
"We had an amazing stay at the lake house. The home is beautiful inside and out, and there is every amenity you could think of, from cooking and cleaning supplies to extra towels and blankets. The view of the lake is stunning and we enjoyed the peace and quiet of the little community. Linh is an excellent host and helped answer all of our questions. We will definitely be back!"
United States
Angel R.
The price is HK$2,040
HK$4,294 total
includes taxes & fees
23 Sept - 24 Sept
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
3 bedrooms, desk, iron/ironing board, travel cot

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

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (20 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is HK$1,292
HK$3,723 total
includes taxes & fees
29 Sept - 30 Sept
Local Artist Inspired | Walk to WestPoint + King Bed
Smart TV, video games, DVD player, books

12. '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, (7 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 HK$1,590
HK$3,093 total
includes taxes & fees
15 Sept - 16 Sept
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Dining

13. 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 HK$1,496
HK$2,940 total
includes taxes & fees
4 Oct - 5 Oct
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Interior

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 HK$2,124
HK$3,657 total
includes taxes & fees
22 Sept - 23 Sept
Lovely 3BR Home with parking-Walk to WP Gate!
TV

15. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean and modern with good amenities. Would stay here again. "
United States
Daniel C.
The price is HK$2,248
HK$3,535 total
includes taxes & fees
22 Sept - 23 Sept
Walk to WP Gate + Free Parking!
Smart TV

16. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (48 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
The price is HK$1,059
HK$2,315 total
includes taxes & fees
14 Sept - 15 Sept
Grant - A Tranquil One Bedroom Steps from River
Interior

17. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is HK$1,537
HK$1,781 total
includes taxes & fees
23 Sept - 24 Sept
Harriman Outdoor Center - Mountain Laurel Cabin
Exterior detail

18. 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 HK$2,075
HK$3,494 total
includes taxes & fees
14 Sept - 15 Sept
Fabulous 3bdrm Home w/parking!
Exterior

19. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is HK$644
HK$744 total
includes taxes & fees
5 Oct - 6 Oct
1 Queen Bed | Non-Smoking, Kitchen
Exterior detail

20. Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi

Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Highland Falls
9.6 out of 10, Exceptional, (36 reviews)
"Good location and had a great stay!"
United States
James M.
The price is HK$2,572
HK$4,558 total
includes taxes & fees
13 Sept - 14 Sept
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Peekskill Hotel Reviews

Tarrytown House Estate

Tarrytown House Estate

8/10 Good
"Very far distance from parking to rooms and lots of areas with only steps not elevators. Hard work carrying bags in if you are staying in certain areas. Otherwise very nice place."
Nicole 1-night trip
Posted 1 hour ago
Tarrytown House Estate

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 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.