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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Peekskill vacation rentals

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

1. 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 SAR 845
SAR 1,576 total
includes taxes & fees
30 Sep - 1 Oct
Contemporary Cozy Cottage
A house with a view of a bridge and mountains.

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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is SAR 743
SAR 1,189 total
includes taxes & fees
30 Sep - 1 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

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 SAR 581
SAR 1,111 total
includes taxes & fees
4 Oct - 5 Oct
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

4. '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 SAR 716
SAR 1,425 total
includes taxes & fees
1 Oct - 2 Oct
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A stone staircase leading to a house with a stone wall and a metal gate.

5. 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, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is SAR 939
SAR 1,499 total
includes taxes & fees
30 Sep - 1 Oct
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

6. 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 SAR 626
SAR 1,292 total
includes taxes & fees
4 Oct - 5 Oct
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

7. 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 SAR 1,248
SAR 2,273 total
includes taxes & fees
7 Oct - 8 Oct
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

8. 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 SAR 432
SAR 1,087 total
includes taxes & fees
1 Oct - 2 Oct
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

9. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (13 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 SAR 469
SAR 1,421 total
includes taxes & fees
30 Sep - 1 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A deck with Adirondack chairs, a fire pit, and a grill.

10. 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 SAR 796
SAR 1,503 total
includes taxes & fees
6 Oct - 7 Oct
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

11. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
Nyc-area Escape Near River, Trails & Mta!
The exterior of Highland Falls Library with a white facade, two wooden benches in front, and a sign above the entrance.

12. 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 SAR 1,874
SAR 2,940 total
includes taxes & fees
11 Oct - 12 Oct
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

13. NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is SAR 879
SAR 2,981 total
includes taxes & fees
21 Oct - 22 Oct
NYC-Area Escape Near River, Trails & MTA!
A wooden coffee table with two decorative planters in a living room.

14. 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 SAR 546
SAR 982 total
includes taxes & fees
30 Sep - 1 Oct
Walk to WP Gate + Free Parking!
A bedroom with a bed, a ceiling fan, a window, and a painting on the wall.

15. 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 SAR 522
SAR 1,576 total
includes taxes & fees
6 Oct - 7 Oct
Local Artist Inspired | Walk to WestPoint + King Bed
Living area

16. 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 SAR 497
SAR 880 total
includes taxes & fees
30 Sep - 1 Oct
Cozy 1-bedroom retreat minutes from West Point!
A wooden cabin with large windows, a wooden bench, and a view of the forest.

17. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is SAR 736
SAR 820 total
includes taxes & fees
4 Oct - 5 Oct
Harriman Outdoor Center - Mountain Laurel Cabin
A hallway with a wooden door, a black table with a sign, and large green plants.

18. 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 SAR 451
SAR 1,606 total
includes taxes & fees
6 Oct - 7 Oct
3BR Near West Point | Coffee Bar | Sleeps 6
A wooden cabin with large windows, a wooden bench, and a view of the forest.

19. Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is SAR 916
SAR 1,000 total
includes taxes & fees
30 Sep - 1 Oct
Harriman Outdoor Center - Cranberry Cabin
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

10/10 Excellent
"Clean and nice place. Plenty of options to eat on-site."
Chad 2-night trip
Posted 1 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.