
House holiday rentals in Peekskill
Find and book unique houses on Airbnb
Top-rated house rentals in Peekskill
Guests agree: these houses are highly rated for location, cleanliness and more.

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.

Lady Montgomery
Enjoy our trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge trail to Beacon and Newburgh waterfront. Perfect for friends and couples who want to explore all that the Hudson Valley has to offer. Enjoy shopping, farms,hiking or dining. Equipped with an outdoor patio, fireplace, fire pit and 2 bikes to help you explore the area. Everyone will enjoy their time in this comfortable artistic home

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

Cozy 3 bedroom house on quiet private road
3 bedroom house overlooking creek on a quiet, private road. Minutes from Metro North Railroad, Hudson River, historic Cold Spring Village, Highlands Country Club golf course, Beacon, downtown Peekskill, Bear Mountain State Park, Boscobel House & Gardens, Fahenstock St Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $80 per stay. I live close by so I’m available for help or assistance during your stay.

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.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Peaceful Yellow Door Cottage
Yellow Door Cottage is a quiet family getaway nestled in the woods, but close to the historic Village of Cold Spring. Large backyard, ideal for afternoon lunch on the deck or an evening around the fire. Located on a lovely country road, great for walking and biking. 3 comfy bedrooms with linens supplied. Wi-Fi, TVs, washer/dryer, close to amazing hikes and the beautiful Hudson River! Rent alone or pair with my cottage next door: Cheerful Private 3 Bedroom Cottage in Cold Spring on Airbnb.

Tranquil Tree-House on the beautiful Hudson River
Take it easy at this unique and tranquil getaway. I look forward to hosting you. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door. We have added a separate kitchenette additional crockpot and induction cooktop.

River & Mtn Views - Jacuzzi - near Metro North
Panoramic Hudson River and Storm King Mountain views, just a 5-minute walk from train station, 3 minutes to Dia Beacon. Walk to Main Street. (Or ride one of the house bikes!) Watch the sun set over the Hudson River from the Jacuzzi (or the outdoor shower) at this prime location. My kitchen is fully equipped with more than just basics. Also, Weber grill out on the deck is hooked to gas line. Includes Linens, Towels & Toiletries. House also has Iron, Ironing Board and Hair Dryer.

Hillside Views in Hudson Valley
Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Cozy, Modern Retreat in the Woods of Cold Spring
Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.
Spectacular Lake Views from Every Room & Garden
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.
Popular amenities for house rentals in Peekskill
House rentals with a pool

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

4Br Mountain Brook House on 130 acres w/ trails

Scenic River View Escape | New Paltz

Midcentury Modern ZenHouse Sculptor Studio

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

Upstate Modern Scandinavian Barn in the Catskills

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Weekly house rentals

Mindful Escape: Theater, Trails, Wood Stove

Slate Cabin - Stylish Country Escape x Rhinebeck

Beautiful Warwick Holiday Escape!

Lakeview Estate - Chef's Kitchen - NYC Getaway

Gingerbread House- a 1950s Catskills Chalet

Architect's Hudson Valley Home in the Woods

This New House

Cozy guest suite bedroom plus living room
Private house rentals

Elegant Hideaway: Cozy Cottage in Katonah, NY

Chic Cozy Upstate Cabin Just 1 Hr From NYC!

Victorian Eclectic

Hudson Valley Bungalow Retreat ~1 hr from NYC

5bed 3.5bath spacious and private with game room

A nice place to getaway

Modern, sun-filled farmhouse retreat

Private Suite in the Heart of the Hudson Valley
Quick stats about house rentals in Peekskill

Total holiday rentals
Explore 20 holiday rentals in Peekskill

Nightly prices starting at
Peekskill holiday rentals start at $76 SGD per night before taxes and fees

Verified guest reviews
Over 1,020 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Peekskill holiday rentals include wifi 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
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Grand Central Terminal
- New York Public Library Main Branch
- Brooklyn Bridge
- New York University
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Old Glory Park
- Mountain Creek Resort
- Ohel Chabad-Lubavitch
- Bronx Zoo
- Yankee Stadium
- Manhattan Bridge
- United Nations Headquarters
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall
- Fairfield Beach
- USTA Billie Jean King National Tennis Center




