Holiday houses in Peekskill
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Top-rated holiday rentals in Peekskill
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Ranch in the Woods | A Peaceful Designer Retreat
Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.
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
Luxe Loft 4 on Main St- Views! Steam Shower! W/D
Welcome to Luxe Studio #4 right on Main Street in Beacon. This is your home base for exploring the beautiful Hudson Valley! Walk to Dia Museum, train, restaurants, shops, galleries, hiking-all at your doorstep! Relaxing, meticulously clean space designed for comfort and indulgence with everything you could need- unforgettable steam shower, full kitchen, washer & dryer. Queen bed with luxe hotel-quality linens. 50” Toshiba 4K Fire TV, hardwood flooring, spacious bathroom with window &toiletries
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
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.
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.
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.
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
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.
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!
The Treecastle at the Roundhouse Homestead
The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill
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
Popular amenities for Peekskill holiday rentals
Other great holiday rentals in Peekskill
Gorgeous Suite w/ Private Entrance
Hudson Valley Home 50 Min from NYC - dog friendly
Modern 3BD West Point USMA House w/ HotTub!
Forest Suite | Croton Dam Trails | 45 Min NYC
Mountainside Home (Beacon/Cold Spring)
Victorian Eclectic
Arkadia House Mid-century retreat with pool & view
Charming 2 bedroom Cottage w/ patio & yard.
When is the best time to visit Peekskill?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $230 AUD | $247 AUD | $218 AUD | $165 AUD | $214 AUD | $208 AUD | $216 AUD | $230 AUD | $228 AUD | $265 AUD | $221 AUD | $195 AUD |
| Avg. temp | 1°C | 2°C | 6°C | 12°C | 18°C | 23°C | 26°C | 25°C | 22°C | 15°C | 10°C | 4°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 holiday rentals in Peekskill
Total holiday rentals
Explore 20 holiday rentals in Peekskill
Nightly prices starting at
Peekskill holiday rentals start at $84 AUD per night before taxes and fees
Verified guest reviews
Over 1,350 verified reviews to help you choose
Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 of Peekskill holiday 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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