Vacation rentals in Peekskill

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Peekskill

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Cortlandt

5.0 out of 5 average rating, 104 reviews

Cottage at Peekskill Hollow

Romantic Hudson Valley cottage just 1 hour outside NYC in northern Westchester! Beautiful, wooded location along the Peekskill Hollow Creek - just off the beaten path. You’ll be surrounded by nature and still be a hop, skip and jump away from restaurants, shopping, hiking/bike trails, West Point, the Hollow Brook Golf Club and historic sites (Revolutionary War, Rockefeller, Roosevelt, Underground Railroad). Quick access (by car or train) to/from NYC and greater Hudson Valley. High speed WiFi.

May 9 – 16

G$51,056 GYD per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Sep 27 – Oct 4

G$28,230 GYD per night

Guest favorite

Apartment in Philipstown

4.88 out of 5 average rating, 187 reviews

Foxglove Farm

Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

Sep 24 – Oct 1

G$27,844 GYD per night

Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Oct 4 – 11

G$115,011 GYD per night

Guest favorite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Feb 22 – Mar 1

G$22,205 GYD per night

Guest favorite

Apartment in Peekskill

4.84 out of 5 average rating, 115 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Feb 19 – 26

G$26,781 GYD per night

Guest favorite

Guest suite in Beacon

4.97 out of 5 average rating, 289 reviews

Hiker's nest

This is a cozy room with private forest views and all the basic amenities (small kitchenette). We are located next to the entrance of Mount Beacon park (the free Loop Bus from the station drops you on our corner), a three-minute walk to the trail entrance, and a 25 minute walk to the train station and Main Street. The room is attached to the main house, but you have your own entrance with code access. We live in the main house, so we are here to answer questions or help with your stay.

May 28 – Jun 4

G$21,512 GYD per night

Superhost

Home in Peekskill

4.9 out of 5 average rating, 153 reviews

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

Feb 22 – Mar 1

G$79,243 GYD per night

Guest favorite

Guest suite in Beacon

4.93 out of 5 average rating, 239 reviews

Quiet apartment with garden access, mountain views

Feel at home in our serene village retreat. Spacious, private, and comfortable, with abundant personality and charm provided by our one-of-a-kind artwork and handmade details. Enjoy the mountain views from the living room, and take advantage of our spacious backyard and garden. Located on a quiet street only blocks away from Main Street’s charming shops and restaurants. Perfectly situated for exploring all that the Hudson Valley has to offer.

Oct 6 – 13

G$29,022 GYD per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Feb 18 – 25

G$17,617 GYD per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 109 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Nov 26 – Dec 3

G$25,900 GYD per night

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 393 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

Mar 7 – 14

G$18,980 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Peekskill vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Peekskill's top sights

Blue Mountain Park4 locals recommend

The Peekskill Coffee House15 locals recommend

Paramount Hudson Valley Theater16 locals recommend

Birdsall House19 locals recommend

The Peekskill Brewery38 locals recommend

Nonna's Pizza8 locals recommend

Other great vacation rentals in Peekskill

Guest favorite

Apartment in Beacon

4.93 out of 5 average rating, 139 reviews

Sunny 1 Bedroom

May 5 – 12

G$31,002 GYD per night

Guest favorite

Barn in Mount Kisco

4.91 out of 5 average rating, 539 reviews

NY Rustic Cottage Getaway

Mar 22 – 29

G$32,363 GYD per night

Guest favorite

Apartment in Nelsonville

4.86 out of 5 average rating, 117 reviews

Wooded stream side Retreat

Feb 22 – Mar 1

G$23,785 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 741 reviews

Hudson Valley Tiny House

Jul 5 – 12

G$22,908 GYD per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 677 reviews

Victorian Haven

Feb 9 – 16

G$27,368 GYD per night

Guest favorite

Apartment in New Windsor

4.95 out of 5 average rating, 111 reviews

Private/Spacious Studio. Guest Loyalty Program

Dec 7 – 14

G$25,654 GYD per night

Guest favorite

Guest suite in Fort Montgomery

4.94 out of 5 average rating, 419 reviews

West Point - Mountain Top Suite

Nov 28 – Dec 5

G$41,342 GYD per night

Guest favorite

Guest suite in Putnam Valley

4.91 out of 5 average rating, 33 reviews

Peaceful lake and woodland retreat

Feb 9 – 16

G$21,707 GYD per night

Show all

Quick stats about vacation rentals in Peekskill

Total rentals
30 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.4K reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Peekskill?
Peekskill has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Peekskill?
Yes! Work meets play with ease at over 20 vacation rentals in Peekskill featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Peekskill?
Experience the best of Peekskill with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Peekskill?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Peekskill have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Peekskill have free parking?
Absolutely! We offer over 20 house rentals with free parking in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Peekskill have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Peekskill. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Peekskill have wifi?
Absolutely! We offer over 20 house rentals with wifi in Peekskill. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Peekskill

Top-rated vacation rentals in Peekskill

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Peekskill vacation rentals

Stay near Peekskill's top sights

Other great vacation rentals in Peekskill

Apartment in Beacon

Barn in Mount Kisco

Apartment in Nelsonville

Tiny home in New Paltz

Home in New Paltz

Apartment in New Windsor

Guest suite in Fort Montgomery

Guest suite in Putnam Valley

Quick stats about vacation rentals in Peekskill

Total rentals

Popular amenities

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Peekskill?

Are there vacation rentals with a dedicated workspace in Peekskill?

How much does it cost to stay in house rentals in Peekskill?

What are the most popular amenities for House Rentals in Peekskill?

Do house rentals in Peekskill have a kitchen?

Do house rentals in Peekskill have free parking?

Do house rentals in Peekskill have air conditioning?

Do house rentals in Peekskill have wifi?

Destinations to explore