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

Peekskill Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Peekskill vacation rentals

Coffee/tea maker, fridge, oven, stovetop

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AED 422
AED 1,123 total
includes taxes & fees
18 Oct - 19 Oct
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Terrace/patio

2. 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)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is AED 459
AED 1,485 total
includes taxes & fees
22 Sep - 23 Sep
House on the Babbling Brook- Quiet 2BR + King Bed!
Desk, WiFi (free), bed sheets

3. '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, (3 reviews)
"Great stay!"
United States
Ann S.
The price is AED 502
AED 1,045 total
includes taxes & fees
22 Sep - 23 Sep
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Property grounds

4. 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, (145 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,215 total
includes taxes & fees
22 Sep - 23 Sep
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Smart TV, video games, DVD player, books

5. '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, (8 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 AED 789
AED 1,507 total
includes taxes & fees
24 Sep - 25 Sep
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
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 AED 474
AED 1,550 total
includes taxes & fees
6 Oct - 7 Oct
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 AED 826
AED 1,542 total
includes taxes & fees
30 Sep - 1 Oct
Contemporary Cozy Cottage
TV

8. 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 AED 540
AED 954 total
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom retreat minutes from West Point!
3 bedrooms, desk, iron/ironing board, travel crib

9. 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 AED 511
AED 1,655 total
includes taxes & fees
28 Sep - 29 Sep
Local Artist Inspired | Walk to WestPoint + King Bed
Exterior detail

10. 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)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is AED 580
AED 1,684 total
includes taxes & fees
23 Sep - 24 Sep
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
3 bedrooms, desk, iron/ironing board, WiFi (free)

11. 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 AED 595
AED 1,771 total
includes taxes & fees
29 Sep - 30 Sep
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Dining

12. 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 AED 701
AED 1,377 total
includes taxes & fees
4 Oct - 5 Oct
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Coffee/tea maker, fridge, microwave, oven

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 AED 949
AED 1,535 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
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 AED 980
AED 1,711 total
includes taxes & fees
6 Oct - 7 Oct
Lovely 3BR Home with parking-Walk to WP Gate!
Smart TV

15. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (49 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 AED 496
AED 1,043 total
includes taxes & fees
28 Sep - 29 Sep
Grant - A Tranquil One Bedroom Steps from River
TV

16. 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 AED 503
AED 956 total
includes taxes & fees
22 Sep - 23 Sep
Walk to WP Gate + Free Parking!
Outdoor dining

17. 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 AED 1,047
AED 2,128 total
includes taxes & fees
22 Sep - 23 Sep
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Interior

18. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is AED 720
AED 834 total
includes taxes & fees
22 Sep - 23 Sep
Harriman Outdoor Center - Mountain Laurel Cabin
Exterior detail

19. 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 AED 1,080
AED 1,727 total
includes taxes & fees
6 Oct - 7 Oct
Fabulous 3bdrm Home w/parking!
Outdoor spa tub

20. 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, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is AED 716
AED 1,471 total
includes taxes & fees
22 Sep - 23 Sep
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

8/10 Good
"The hotel is nice, and clean, and they have the BEST big towels. But it doesn't have an actual restaurant or room service, which is very inconvenient. They also seem to have an issue around check-in. I was in a line of like 20 people, which was surprising. There was one desk clerk handling some sort of problem with one guest for 20 minutes. The other clerk moved glacially slow. Neither clerk seemed welcoming or customer service oriented. During this time, the manager came out several times to talk to the clerk handling the problem, but did not even look at or acknowlege the long line of people waiting. I would expect a manager to step in and help process the long line of check-ins. Another person came out several times and told people to use the check-in automatic kiosks, and several people said they had tried it already and it didn't even work. "Oh, sorry about that," she said. There's also a mystifying thing... the hallways and navigation are poorly marked, and it's not easy to figure out where you are going, or find an elevator. I was in a 3xx room, and when I got to the elevator, it said I was on floor 2 (which had the 4xx rooms). In the elevator, I had to press 1 to get to the floor with the 3xx rooms. ????? Didn't make sense! My recommendations: More check-in staff, better customer service training, and better signage for navigation."
Mary 1-night trip
Posted less than an hour ago
Sleepy Hollow Hotel, a Dolce by Wyndham

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.