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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, 224 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
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, 174 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 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
4.79 out of 5 average rating, 213 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, 216 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 favorite
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, 162 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.

Guest favorite
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
4.95 out of 5 average rating, 121 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.

Guest favorite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.98 out of 5 average rating, 382 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

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, 537 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. $19 cleaning with or without pets.

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, 163 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
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley
4.95 out of 5 average rating, 122 reviews

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

Top guest favorite
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
4.97 out of 5 average rating, 231 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 favorite
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
4.97 out of 5 average rating, 115 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 vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Peekskill

Top guest favorite
Apartment in Stony Point
4.97 out of 5 average rating, 96 reviews

Gorgeous Suite w/ Private Entrance

Superhost
A cozy seating area features a gray sectional sofa adorned with soft pillows. A glass coffee table sits at the center, complemented by a decorative basket. The floor is covered with a large area rug featuring a leaf design, enhancing the inviting atmosphere.
Cottage in Putnam Valley
4.9 out of 5 average rating, 39 reviews

Hudson Valley Home 50 Min from NYC - dog friendly

Guest favorite
A spacious living area exhibits warm wooden floors and large windows adorned with decorative curtains. A cozy futon is positioned on a textured rug, complemented by a decorative welcome sign on the wall. A spiral staircase leads to the upper level, enhancing the open layout.
Apartment in Stony Point
4.88 out of 5 average rating, 214 reviews

E and T Getaway LLC

Top guest favorite
A spacious living area showcases a neutral color palette, complemented by a dark sofa and a decorative area rug. An air conditioning unit and wall art pieces add character, while natural light filters in through a large window. Red accent furniture enhances the inviting atmosphere.
Guest suite in Croton-on-Hudson
4.93 out of 5 average rating, 55 reviews

Forest Suite | Croton Dam Trails | 45 Min NYC

Guest favorite
A comfortable living room features a mix of seating options, including a patterned armchair and a bright blue couch. A small wooden coffee table sits at the center, surrounded by an area rug. Natural light enters through large windows, enhancing the space's inviting feel.
Home in Peekskill
4.93 out of 5 average rating, 28 reviews

Victorian Eclectic

Guest favorite
A serene outdoor setting features a sparkling swimming pool surrounded by lush greenery. Comfortable seating areas, including deck chairs, are positioned nearby. Hammocks hang between trees, providing a relaxing retreat. Scenic views of the Hudson River and mountains enhance the tranquil atmosphere.
Home in Philipstown
4.95 out of 5 average rating, 37 reviews

Arkadia House Mid-century retreat with pool & view

Guest favorite
Apartment in Peekskill
4.85 out of 5 average rating, 13 reviews

Peekskill apartment in the center of downtown

Superhost
The exterior of the cottage is shown with a welcoming porch featuring a red umbrella over a dining table. Potted plants are arranged along the walkway, while a grill and a trash bin are visible nearby. Lush greenery surrounds the property, enhancing the serene environment.
Guesthouse in Cortlandt
4.87 out of 5 average rating, 94 reviews

Charming 2 bedroom Cottage w/ patio & yard.

When is the best time to visit Peekskill?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$34,508 GYDG$37,017 GYDG$32,626 GYDG$24,678 GYDG$31,998 GYDG$31,162 GYDG$32,416 GYDG$34,508 GYDG$34,090 GYDG$39,736 GYDG$33,044 GYDG$29,279 GYD
Avg. temp1°C2°C6°C12°C18°C23°C26°C25°C22°C15°C10°C4°C

Frequently Asked Questions

  • What are the best places to stay in Peekskill?

    Many travelers choose accommodations near Peekskill’s historic downtown for easy access to shops, dining, and river views. Areas around the waterfront and local parks are also frequently suggested for scenic surroundings.

  • What are the best things to do in Peekskill with kids?

    Families explore Peekskill Riverfront Green Park for playgrounds and open space, or visit local art workshops and interactive exhibits at Hudson Valley MOCA. Seasonal events and public performances add variety for children year-round.

  • What are some of the best things to do in Peekskill?

    Stroll the Peekskill Riverfront Green Park, see contemporary works at Hudson Valley MOCA, or attend a show at the Paramount Hudson Valley Theater. Hiking, dining, and exploring local galleries give visitors a taste of the city’s creative energy.

  • How is the weather in Peekskill?

    Peekskill experiences cold winters around 29–40°F (-2–5°C), and warm, humid summers reaching 72–86°F (22–30°C). Most rain falls from spring through late summer, so bring a waterproof layer if visiting then.

  • When is the best time to visit Peekskill?

    Late spring and early autumn are often recommended for comfortable temperatures, river views, and colorful foliage. Summer has outdoor festivals and lively waterfront activities, while winter is quieter and cooler.

  • What are the best places to visit in Peekskill?

    Explore the Peekskill Waterfront for Hudson River views, and visit the Paramount Hudson Valley Theater for performances. The Hudson Valley MOCA has contemporary art exhibitions that draw art lovers year-round.

  • What are some hiking trails in Peekskill?

    Blue Mountain Reservation has several hiking and biking trails through forests and ridges. Locals also frequent Depew Park for scenic paths, birdwatching, and gentle woodland walks.

  • What are some family activities we can do in Peekskill?

    Families enjoy playgrounds and open fields at Depew Park, boat watching and picnics at Riverfront Green Park, and hands-on art or theater workshops held throughout the city.

  • What are some of the best day trip ideas from Peekskill?

    Explore Hudson Valley wineries, historic estates, or the contemporary art at Dia Beacon near Peekskill. Outdoor enthusiasts often visit Bear Mountain State Park or the Appalachian Trail for hiking and scenic views.

  • Are there any pet friendly accommodations available in Peekskill?

    Peekskill has pet-friendly vacation rentals, with many welcoming dogs and cats. Check for listings with outdoor spaces or proximity to parks, and always review each host’s pet policy for specific guidelines.

  • What are some local tips for visiting Peekskill?

    Arrive early at Peekskill’s riverfront for sunrise views and easier parking, and check local listings for pop-up markets, gallery shows, and live performances. Sampling locally roasted coffee and chatting with shop owners adds a friendly touch to your stay.

  • What is Peekskill known for?

    Peekskill is known for its Hudson River setting, thriving arts community, and historic downtown. The city often draws visitors to its theaters, galleries, and scenic parks.

  • What are the best hidden gems to explore in Peekskill?

    Peekskill has small art studios nestled in its downtown, historic murals that reflect local stories, and creative coffee shops that highlight area artists. Wandering the waterfront at Charles Point Pier Park reveals scenic spots often appreciated by locals.

  • What are the best foods to try in Peekskill?

    Peekskill has New York-style pizza, locally brewed craft beer, and farm-to-table dishes inspired by Hudson Valley produce. Local bakeries and cafes serve freshly baked goods and small-batch coffee.

  • What should I bring for a trip to Peekskill?

    Pack comfortable walking shoes for exploring downtown, a light rain jacket in spring and summer, and warm layers for winter visits. Bring a camera to capture riverfront sunsets and artwork around the city.

  • What is the nightlife in Peekskill like?

    Peekskill has locally owned bars, inviting breweries, and live music venues, especially around the waterfront and downtown. Locals gather for craft beer, open mic nights, and performances in casual settings.

  • What are the most popular events or festivals in Peekskill?

    Peekskill hosts street fairs in summer, seasonal farmers markets, and art festivals around downtown. The Hudson Valley Irish Fest in early autumn and music events at the Paramount Hudson Valley Theater are frequently suggested.

  • Are there family friendly vacation rentals in Peekskill?

    Peekskill has family-friendly rentals, including homes with multiple bedrooms, kitchens, and outdoor spaces. Look for listings near parks or the waterfront for convenient access to playgrounds and walking trails.

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$12,548 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • 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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