Hudson River panorama, Henry Hudson Park

Peekskill Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Peekskill vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Private Country Getaway

Private Country Getaway
Bedford Hills
9.6 out of 10, Exceptional, (4 reviews)
"We had a busy and lovely weekend to attend and be part of my nieces wedding. The location was perfect and the property is beautiful. Kitchen was perfect for gathering in the morning and the great room was big and comfy for catching up! "
United States
Karin R.
The price is AED 3,306
AED 5,887 total
includes taxes & fees
15 Aug - 16 Aug
Private Country Getaway
TV, fireplace

2. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AED 826
AED 1,548 total
includes taxes & fees
9 Aug - 10 Aug
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Dining

3. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is AED 3,140
AED 4,045 total
includes taxes & fees
8 Aug - 9 Aug
Prime Luxe 3-BR NYC - Free Parking
Luxury Villa, Garden View | Dining

4. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is AED 1,488
AED 2,314 total
includes taxes & fees
8 Aug - 9 Aug
Luxury NYC Home with Free Parking for 12
Luxury Apartment | In-room dining

5. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
The price is AED 3,306
AED 4,229 total
includes taxes & fees
8 Aug - 9 Aug
3BR Prime Luxury NY - Free Parking
Living area

6. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is AED 3,306
AED 5,037 total
includes taxes & fees
8 Aug - 9 Aug
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
Luxury Apartment | Private kitchen

7. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is AED 658
AED 1,300 total
includes taxes & fees
8 Aug - 9 Aug
Elegant Hideaway with Free Parking
Smart TV

8. Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is AED 1,980
AED 3,273 total
includes taxes & fees
8 Aug - 9 Aug
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
3 bedrooms, iron/ironing board, internet, bed sheets

9. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is AED 1,818
AED 3,067 total
includes taxes & fees
8 Aug - 9 Aug
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Villa, Garden View | Living area

10. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is AED 1,818
AED 2,627 total
includes taxes & fees
8 Aug - 9 Aug
Luxury NYC Home Game Room Free Parking
Private kitchen

11. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
White Plains
The price is AED 1,818
AED 3,067 total
includes taxes & fees
8 Aug - 9 Aug
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
Smart TV, fireplace, video games, DVD player

12. Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is AED 1,980
AED 3,583 total
includes taxes & fees
10 Aug - 11 Aug
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Property grounds

13. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.2 out of 10, Wonderful, (5 reviews)
"It was excellent!! "
United States
Henry C.
The price is AED 676
AED 1,252 total
includes taxes & fees
6 Sep - 7 Sep
Garden Loft with Patios & Green Space · Westchester Retreat
Interior

14. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is AED 893
AED 1,198 total
includes taxes & fees
8 Aug - 9 Aug
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
3 bedrooms, iron/ironing board, internet, bed sheets

15. Spacious 3BR Home • Free Parking • Ideal for Families & Groups • Easy NYC Access

Spacious 3BR Home • Free Parking • Ideal for Families & Groups • Easy NYC Access
White Plains
The price is AED 2,050
AED 3,394 total
includes taxes & fees
11 Aug - 12 Aug
Spacious 3BR Home • Free Parking • Ideal for Families & Groups • Easy NYC Access
Property grounds

16. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.4 out of 10, Exceptional, (10 reviews)
"Such a lovely cabin - so many details to make for an incredible stay. Amazing location - lake, mountains! Wylda was wonderful."
United States
Clare
The price is AED 716
AED 1,270 total
includes taxes & fees
13 Aug - 14 Aug
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
House | 5 bedrooms

17. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AED 2,925
AED 5,030 total
includes taxes & fees
1 Sep - 2 Sep
Summer Pool Oasis Custom Bar Arcade Pool Table
Outdoor banquet area

18. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.6 out of 10, Excellent, (8 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is AED 2,498
AED 4,459 total
includes taxes & fees
10 Aug - 11 Aug
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Interior

19. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is AED 782
AED 998 total
includes taxes & fees
9 Aug - 10 Aug
1BR Queen near NYC | Trails, Biking & Sauna Bliss
Exterior

20. 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 AED 386
AED 727 total
includes taxes & fees
10 Aug - 11 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

10/10 Excellent
"The staff here is amazing, even though the computer crashed I was getting married that weekend. I had three rules with two king size beds, and all of them confirmed then no rule. The hotel was so overbooked. The police had to come twice with some lunatic but overall it’s an amazing place. The staff end over."
Henrietta 2-night trip
Posted less than an hour ago
Hilton Garden Inn Westchester Dobbs Ferry, NY

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 Depew Park, or simply take in cultural attractions like Paramount Hudson Valley Theater and Peekskill Museum. Other places in town to visit include Dramatic Hall and Lincoln Depot Museum.

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.