Vacation rentals in Peekskill

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Top-rated vacation rentals in Peekskill

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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

Jul 6 – 13

G$30,085 GYD per night

Superhost

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.

Aug 6 – 13

G$29,172 GYD per night

Superhost

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.

Jan 12 – 19

G$26,976 GYD per night

Superhost

Cottage in Putnam Valley

4.9 out of 5 average rating, 213 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Jul 20 – 27

G$54,613 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 18 – 25

G$79,456 GYD per night

Guest favorite

Guest suite in Peekskill

4.94 out of 5 average rating, 117 reviews

Spa themed suite w/private entrance, and king bed!

This stunning spa-themed private oasis in the heart of Peekskill epitomizes peace and serenity. The suite with its own private entrance boasts a king size bed, tranquil workspace, Amazon Fire TV Stick, high speed internet, bathroom with spa-like shower, bar, & kitchenette w/coffee, tea, water, & snacks. The accent water features, trees, & lighting has an eclectic way of bringing nature & the outdoors to this unique space. Read your favorite book or relax on the patio!

Jul 21 – 28

G$33,139 GYD per night

Guest favorite

Apartment in Ossining

4.94 out of 5 average rating, 297 reviews

Hudson River Peaceful Getaway

Self check-in and private entrance. Parking for two cars. Peaceful apartment on the Hudson River. Train to NYC (Scarborough Station) is an 8 minute walk through historic neighborhood. Arcadian Mall (Grocery store, Starbucks, etc) 5 minute walk. Rivers views from inside and from three patios (1 on entrance side, 2 on River side). We only allow declawed cats because they can scratch and damage our expensive furniture and carpets. Most house trained dogs are welcome :)

Sep 15 – 22

G$59,839 GYD per night

Guest favorite

Earthen home in Ossining

4.87 out of 5 average rating, 143 reviews

The Babbling Brook

Unique 2 room and 3rd room ( full bath) with backyard and babbling brook with 5 minute ride to train into NYC and 45 minute car ride to midtown Manhattan (with no traffic, lol) Totally renovated with gorgeous large bedroom overlooking backyard and brook. Private entrance with patio. Private driveway with parking spot. For 1 night only guests add $15.00 cleaning fee. Here is a 2 minute Video of "THE BABBLING BROOK" https://www.youtube.com/watch?v=CRUac3qSOm0

May 4 – 11

G$26,831 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.

Jul 24 – 31

G$30,808 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:)

Jan 17 – 24

G$17,664 GYD per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 106 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 14 – 21

G$26,172 GYD per night

Guest favorite

Loft in Cornwall

4.86 out of 5 average rating, 390 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!

Oct 15 – 22

G$19,031 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 Brewery39 locals recommend

Nonna's Pizza8 locals recommend

Other great vacation rentals in Peekskill

Guest favorite

Cottage in Cortlandt

5.0 out of 5 average rating, 103 reviews

Cottage at Peekskill Hollow

Jan 3 – 10

G$51,574 GYD per night

Guest favorite

Apartment in New Windsor

4.95 out of 5 average rating, 110 reviews

Quiet/Private/Spacious Studio. Balcony. Parking.

Dec 2 – 9

G$25,757 GYD per night

Guest favorite

Guest suite in Fort Montgomery

4.94 out of 5 average rating, 418 reviews

West Point - Mountain Top Suite

Feb 22 – Mar 1

G$41,422 GYD per night

Guest favorite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

Adorable Guest Apartment in Victorian Mansion

Mar 7 – 14

G$22,448 GYD per night

Guest favorite

Guest suite in Beacon

4.97 out of 5 average rating, 289 reviews

Hiker's nest

May 7 – 14

G$21,570 GYD per night

Guest favorite

Home in Wappingers Falls

4.98 out of 5 average rating, 102 reviews

Tranquil Tree-House on the beautiful Hudson River

Oct 6 – 11

G$32,905 GYD per night

Guest favorite

Tiny home in Cold Spring

5.0 out of 5 average rating, 239 reviews

Tiny house on tiny farm close to hiking trails.

Jul 2 – 9

G$29,031 GYD per night

Guest favorite

Apartment in Croton-on-Hudson

4.98 out of 5 average rating, 267 reviews

Luxury 2bd⭐Comfort+Style⭐

Feb 23 – Mar 2

G$43,427 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 20 homes with air conditioning, over 10 homes with a kitchen, over 20 homes with free parking, over 20 homes with wifi, 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

Cottage in Cortlandt

Apartment in New Windsor

Guest suite in Fort Montgomery

Guest suite in Chester

Guest suite in Beacon

Home in Wappingers Falls

Tiny home in Cold Spring

Apartment in Croton-on-Hudson

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