Holiday houses in Peekskill

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Top-rated holiday rentals in Peekskill

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

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Guest favourite
The exterior of the house is set among lush greenery and features a large elevated deck that wraps around the structure. Large windows provide natural light, and the building is supported by a prominent boulder, blending harmoniously with the surrounding forest.
Home in Ossining
4.86 out of 5 average rating, 160 reviews

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Top Guest favourite
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, 219 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 favourite
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, 153 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

Guest favourite
A private patio space is featured, furnished with comfortable seating and a dining table. An umbrella provides shade over the table, while warm string lights enhance the ambiance. Surrounding greenery creates a serene backdrop, and a barbeque is positioned nearby for outdoor cooking.
Apartment in Peekskill
4.81 out of 5 average rating, 200 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.

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, 212 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.

Guest favourite
A spacious living area features a light-colored sectional sofa adorned with a patterned throw and decorative pillows. Soft carpeting covers the floor, enhancing comfort. Natural light floods the space through large windows, illuminating the surrounding decor, including framed photographs on the walls.
Guest suite in Croton-on-Hudson
4.92 out of 5 average rating, 155 reviews

The Bluestone - Spacious 2 bedroom w/central air

Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: No Kitchen!! Drive, walkway & entrance accessible to full size wheelchair (see photos) but bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

Top Guest favourite
A spacious living area is designed with tall windows dressed in yellow curtains, allowing natural light to fill the room. A blue sofa with accent pillows is positioned near a round mirror. A dining table and chairs offer a comfortable space for meals, complemented by a Smart TV on a stand.
Place to stay in Beacon
4.96 out of 5 average rating, 630 reviews

Luxe Loft 1 on Main St.- Steam Shower! Views! W/D

Located on Beacon’s Main St The Luxe Loft Studios place you in the heart of it all just steps from the Metro North train, Dia Museum, top restaurants, galleries & shopping. Designed for relaxation & rejuvenation, each studio offers an indulgent steam shower, a fully equipped kitchen with Keurig and complimentary coffee and tea, bottled water, Smart TV, a queen-size bed with hotel-quality linens, and a Samsung washer and dryer. Explore Beacon and the Hudson Valley with ease no car required.

Guest favourite
A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.
Home in Putnam Valley
4.98 out of 5 average rating, 104 reviews

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

Top Guest favourite
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, 502 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.

Guest favourite
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, 159 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!

Top Guest favourite
A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.
Cottage in Putnam Valley
4.96 out of 5 average rating, 214 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

Top Guest favourite
A single-story home in a vibrant pink hue showcases a unique oval front door, flanked by dark shutters. A concrete pathway leads to the entrance, surrounded by a well-maintained green lawn and partial wooden fencing in the background.
Home in Peekskill
4.99 out of 5 average rating, 101 reviews

Charming Home in Peekskill NY

Enjoy this stylish home located less than a 10 minute drive from many walking/biking trails and tons of restaurants and local entertainment. It is also a 2 minute drive from the NY Presbyterian Hudson Valley Hospital perfect for Traveling Nurses and other short-term healthcare professionals. The neighborhood is quiet and situated at the end of a cul-de-sac, so there is no through traffic, suitable for walking your dog.

Popular amenities for Peekskill holiday rentals

When is the best time to visit Peekskill?

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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.

  • 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.

  • 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.

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

    Yes! Work meets play with ease at over 10 vacation rentals in Peekskill featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Peekskill?

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

  • 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 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 wifi?

    Absolutely! We offer over 20 house rentals with wifi 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.

  • 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 wifi, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Peekskill

  • Total holiday rentals

    Explore 30 holiday rentals in Peekskill

  • Nightly prices starting at

    Peekskill holiday rentals start at $85 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Peekskill holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Peekskill rentals

  • 4.7 Average rating

    Peekskill stays receive an average rating of 4.7 out of 5 from guests

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