Vacation rentals in Peekskill

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Top-rated vacation rentals in Peekskill

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

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Top guest favorite
A quaint cottage is nestled among trees, featuring a covered porch with a railing. Colorful seasonal flowers adorn the entrance, leading to a gravel pathway. The driveway is lined with trees and offers ample parking space, creating a serene atmosphere in a wooded setting.
Cottage in Cortlandt
5 out of 5 average rating, 209 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

Top guest favorite
The sleeping area features two spacious beds, each with coordinating linens in calming green tones. Warm light is provided by two bedside lamps, enhancing a cozy ambiance. A decorative ottoman and a circular rug add texture and comfort to the inviting space.
Guest suite in New Windsor
4.96 out of 5 average rating, 252 reviews

Artistic Loft Private Home baked goodies

Features - 2 Super comfy queen sized beds. 2 Twin - Huge bathroom - Tub - Seated shower -Coffee/Tea/Snacks/Morning Muffins - Kitchenette - Private driveway. Parking at door. - Dedicated work desk. Wifi -Single traveler discount - Extra guest fee over 2 guests - 5 min SKAC -12 min USMA -10 min Woodbury Common -15 min Newburgh Riverfront Restaurants -25 min Beacon -35 min Bethel -Must be 25 years or older to book. No parties or gatherings. -6 guest maximum (inquire) -No 3rd party bookings

Top guest favorite
A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.
Home in Putnam Valley
4.99 out of 5 average rating, 133 reviews

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Superhost
A tranquil outdoor deck features two yellow Adirondack chairs facing the Hudson River. The landscape includes distant mountains and a picturesque sunset casting warm colors across the sky, reflecting on the calm water.
Home in Peekskill
4.89 out of 5 average rating, 205 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, the train is loud, 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.

Top guest favorite
A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.
Apartment in Ossining
4.96 out of 5 average rating, 472 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Top guest favorite
Apartment in Newburgh
4.88 out of 5 average rating, 217 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Guest favorite
A charming cabin with a red exterior is nestled among tall trees and autumn foliage. The building features multiple windows and a staircase leading to the entrance, while a rock border surrounds the lush ground cover and fallen leaves.
Cabin in Putnam Valley
4.94 out of 5 average rating, 144 reviews

Sweet, stylish cabin in the woods- hiking & more!

Only an hour north of NYC, but a world away! Adorable cabin in the woods offering stylish updated decor and beautiful natural surroundings. Brand new and completely renovated interior, but all the classic charm of the country. Trade in skyscrapers for tall trees in this sweet country escape that is near Fahnestock Park (surrounded by great hiking, skiing, etc) and 15m from the village of Cold Spring. Fully set up w/ wifi, Netflix & more! Quiet, considerate guests only please!

Guest favorite
A well-lit living area features a gray sofa adorned with decorative cushions and a coffee table positioned on a patterned area rug. Natural light enters through a window, illuminating the space. A small desk is located near the entrance, complemented by a welcoming front door.
Apartment in Mohegan Lake
4.81 out of 5 average rating, 186 reviews

Yellow House one bedroom

Recently updated cozy, clean and quiet 1 bedroom apartment with private entrance and parking. Breakfast bar w/ complementary coffee & herbal tea selection. Generous selection of books, movies & music CDs. Well lit living area and kitchen w/ reduced light in bedroom. Just a few minutes walk to Mohegan Lake and Sylvan Glen nature trail. Conveniently located near major highways, metro north train, area restaurants and shopping, popular event venues and outdoor attractions.

Top guest favorite
A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.
Guesthouse in Cold Spring
4.99 out of 5 average rating, 190 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

Top guest favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 100 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Top guest favorite
Large triangular windows provide a view of the snowy landscape outside, allowing natural light to fill the space. The wood-paneled walls and ceiling create a warm ambiance, while a minimalist chandelier hangs above, adding a touch of modern design.
Guest suite in Marlboro Township
4.96 out of 5 average rating, 224 reviews

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.

Guest favorite
An open studio layout features a dining island with black chairs, a cozy couch in the corner, and a spacious bed made with neutral bedding. Decorative walls showcase intricate designs, while numerous pendant lights hang from the ceiling, illuminating the area. Large windows provide natural light.
Guesthouse in Peekskill
4.93 out of 5 average rating, 294 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Popular amenities for Peekskill vacation rentals

When is the best time to visit Peekskill?

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Avg. priceG$27,415 GYDG$26,159 GYDG$23,648 GYDG$24,694 GYDG$32,019 GYDG$31,182 GYDG$33,065 GYDG$31,391 GYDG$29,507 GYDG$33,065 GYDG$26,159 GYDG$26,159 GYD
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Frequently Asked Questions

  • Are there family-friendly house rentals in Peekskill?

    Peekskill has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there house rentals with a dedicated workspace in Peekskill?

    Yes! Work meets play with ease at over 10 house 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 free parking, over 10 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Where should I stay in Peekskill?

    Make yourself at home in Peekskill by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Pleasantside, and over 120 vacation rentals in Peekskill.

  • 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.

  • Are there pet-friendly vacation rentals in Peekskill?

    Four-legged friends are welcome in Peekskill. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Peekskill have free parking?

    Absolutely! We offer over 10 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.

Quick stats about vacation rentals in Peekskill

  • Total vacation rentals

    Explore 20 vacation rentals in Peekskill

  • Nightly prices starting at

    Peekskill vacation rentals start at G$12,556 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,580 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Peekskill vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Peekskill rentals

  • 4.8 Average rating

    Peekskill stays are highly rated by guests—averaging 4.8 out of 5!

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