
Family-friendly holiday rentals in Philipstown
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Philipstown

Total holiday rentals
Explore 220 holiday rentals in Philipstown

Nightly prices starting at
Philipstown holiday rentals start at $128 SGD per night before taxes and fees

Verified guest reviews
Over 11,980 verified reviews to help you choose

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
220 of Philipstown holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Philipstown rentals

4.9 Average rating
Philipstown stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated family-friendly rentals in Philipstown
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Foxglove Farm
Peace and tranquility await you at the end of this private road surrounded by forest. My home is a log cabin with a private apartment on the lower level, which includes a patio as well as use of other outdoor spaces. There is a fire pit just past your patio and a short path will put you on the Appalachian Trail. As an herbalist and ethnobotanist, plants are my love and my livelihood. They are an integral part of my life and my home. I welcome you to stroll through the many gardens and paths.

HOT Sauna/COLD Plunge- Mountains-Hiking-NYC Trains
Your SPA - Cedar Barrel HOT SAUNA - Outdoor Cozy updated 1814 Cold Spring Village Classic-NATIONAL Historic Register Close to West Point & Beacon Guest Jack's comments "This apartment gave me the feel that I had my own place in a beautiful river town" Mountain Views - Sunny (12+ Windows) 3 Bedroom Modern Garden Apartment (850+SF) Cozy for 1 to 6 #1 Coffees & Teas Walk to Waterfalls, Hiking Trails, River Beaches, NYC trains Restaurants & cafes Outdoor living space in Garden - birds

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

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.

Bear Mtn Haus near hiking trails
Welcome to our cozy and thoroughly cleaned Garrison cottage steps to Anthony's Nose hiking trail, minutes from the Bear Mountain bridge, just 60min from NYC, 15 min to Cold Spring shops and restaurants, 8 min drive from the Garrison train stop. Set on the mountainside, we have lovely partial views of the Hudson river. Short drive to Woodbury Commons Premium Outlet mall and close to Storm King, and Beacon. Our house is suitable for 6 people, but can accommodate 8 at an extra charge.

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!

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.

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.

Secluded Hilltop Cabin near Beacon & Cold Spring
3 private acres atop small mountain, next to massive forest preserve. 90 min from NYC but feels like you're way upstate. 130+ 5-star reviews! Cozy deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + twin-size mattress day bed on the porch. Fast WiFi. Fire pit and stacks of cut wood. Plus waterfall area with meditation pier (but waterfall only active Apr-Jun) 5 miles from Beacon restaurants & Cold Spring hiking trails.

Historic 1 bedroom home in Cold Spring, NY
This lovingly restored home, built in 1826,is located within the hamlet of Nelsonville within walking distance of the village of Cold Spring. This home has its own entrance and private courtyard and is attached to the owners main residence. Space is curated with antiques and is intended for a couple. This is cozy any time of the year. This home is near trailheads of spectacular hikes in the Hudson Highlands and at the base of Bull Hill.

Modern Country Cottage by Bear Mountain
Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn and explore the 4 acres of most authentic Hudson Valley landscape.

Creekside Home Near Cold Spring & West Point
Private 3BR home overlooking a peaceful creek on a quiet road. Minutes to Cold Spring, Beacon, Peekskill, the Hudson River, Metro-North, West Point, Bear Mountain, and top attractions like Boscobel and Hudson Valley Shakespeare. Close to hiking, golf, restaurants, and farmers markets. Dog-friendly ($80 per stay). Perfect for a relaxing Hudson Valley getaway.
Popular amenities for Philipstown family-friendly rentals
Family-friendly home rentals with a hot tub

Forest Spa Retreat on Cascading Brook • 90 Min NYC

midcentury mod * POOL * walk out trail 2 mohonk

Willow Treehouse - secluded, unique, romantic

Hilltop Hideaway Forest Villa on 13 acres!

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Cozy Mountainside Suite - Minutes from Beacon

Cozy West Point Hide Away and Cadet’s Get Away

West Point Mountain House
Family- and pet-friendly home rentals

West Point/Bear Mountain/Hudson Valley Getaway

Slate Cabin - Stylish Country Escape x Rhinebeck

Creekside cottage on 65 acres of land

The Waterfall House

Top Side

Beacon Creek House

Cozy getaway in Cold Spring

Luxury A-Frame Cabin in the Woods with Sauna
Family-friendly home rentals with a pool

Entire Home (private pool), Event Friendly

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

Private Country Getaway

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

Huge eclectic space w/ private pool. 1.5hr to city

Modern Upstate Cabin, near Rhinebeck NY

Peaceful Light-Filled Guesthouse salt pool/sauna

A Lovely Cottage in the Woods (Pool Open!)
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $399 SGD | $425 SGD | $396 SGD | $383 SGD | $479 SGD | $474 SGD | $466 SGD | $488 SGD | $434 SGD | $461 SGD | $476 SGD | $414 SGD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Rentals with lake access Philipstown
- Rentals with a firepit Philipstown
- Rentals with beach access Philipstown
- Flat rentals Philipstown
- Rentals with an EV charger Philipstown
- Pet-friendly rentals Philipstown
- Rentals with a patio Philipstown
- House rentals Philipstown
- Rentals with a kayak Philipstown
- Rentals with a washing machine and dryer Philipstown
- Rentals with breakfast Philipstown
- Rentals with pools Philipstown
- Rentals with outdoor seating Philipstown
- Rentals with a fireplace Philipstown
- Fitness-friendly rentals Philipstown
- Waterfront rentals Philipstown
- Rentals with a hot tub Philipstown
- Family-friendly rentals Putnam County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Times Square
- Madison Square Garden
- New York City Center
- Central Park Zoo
- New York University
- Columbia University
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- United Nations Headquarters
- Rockefeller Center
- Empire State Building
- Citi Field
- Grand Central Terminal
- Bryant Park
- Radio City Music Hall
- Thunder Ridge Ski Area
- Astoria Park
- Fairfield Beach
- USTA Billie Jean King National Tennis Center
- The Metropolitan Museum of Art
- Prudential Center
- American Dream
- Minnewaska State Park Preserve





