
Holiday rentals with outdoor seating in Highlands
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Highlands
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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.

Tiny glamping cabin with mineral spring hot tub
This off grid, alternative powered site is located towards the front of a large twelve acre estate, alongside a flowing brook. Elevated over a natural spring that flows year round, the Japanese inspired aesthetics of this private, tiny cabin sits perched atop a deck among the wooded trees overlooking the waterway the mineral spring feeds, but not before filling the in-ground, cedar lined, two person, bubbling hot tub heated with a wood burning stove. One of two glamping sites on the 12 acres.

HOT Sauna - Mountain Views - 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

Country Getaway - Close to Hiking & Storm King
Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Ultimate Walking Access to Thayer Gate USMA
Enjoy the Ultimate Walking Access to Thayer Gate from this Beautiful Farmhouse. Fully immerse yourself in the West Point experience! Hosted by a ‘23 Old Grad Mom, this Beautiful Farmhouse greets you with spacious dining room seating for 10 to gather around the table, fully equipped kitchen with granite countertops for all cooking needs, 75” SmartTV, 350 Roku channels, Cold AC and great backyard for entertaining! Allergen free environment. No smoking or pets. No exceptions or loss of deposit.

Secluded mountain top horse property near W. Point
"Green acres is the place to be, farm living is the life for me!" This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 mins from West Pt. situated on a mountain top. This private little space is a nature lovers paradise. Come, watch the horses from the front deck, enjoy fresh eggs in the morning, relax by the outdoor fire pit, star gaze & hike/explore forest trails right out the front door.

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

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.

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.

Lovely, Quiet and Very Private! Entire Loft!
Nestled in the mountains is a peaceful place to lay your head. Just a stones throw from vineyards, brewery's and some of the best views and attractions the Hudson Valley has to offer. Here you'll find a private & secluded bedroom and bathroom fit for 2. A small "kitchenette" is avaliable for use as well as an outdoor seating area with fireplace. Free parking in designated spot. Waterfall is a short hike away.

Mountain View Retreat
15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

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.
Popular amenities for Highlands outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Cozy Riverfront Victorian in the Hudson Valley

Lovely home in town of Newburgh

Tranquil Tree-House on the beautiful Hudson River

Spectacular Lake Views from Every Room & Garden

Slate Cabin - Stylish Country Escape x Rhinebeck

Creekside cottage on 65 acres of land

Mt hikes, city strolls river walks

Hudson Valley Mountaintop Riverview
Apartment rentals with outdoor seating

Foxglove Farm

Charming Lakeside Retreat

E and T Getaway LLC

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

2-Bedroom in COH, near Newburgh & West Point

Hoppy Hill Farm House

Stylish affordable 2BR Steps from Thayer gate+prkg

Warwick Village Apt w Off St Parking 2 GIG WIFI
Condo rentals with outdoor seating

Lovely 1 Bedroom/Pool/Hot Tub/King Bed/Ski In/Out

Premium New 1bd Sunset balcony 3rd flr

Sunsets at Mountain Creek! Walk to ski slopes!

Courtyard Overlook @ Spa Owners Residential Condo

Skiiis N Tees • Mountain Views, Cozy Vibes

BRAND NEW! MODERN SlopeSide Condo, Golf, & Spa

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna

Five-star charming getaway blocks to NYC transit.
Quick stats about holiday rentals with outdoor seating in Highlands

Total holiday rentals
Explore 110 holiday rentals in Highlands

Nightly prices starting at
Highlands holiday rentals start at $135 NZD per night before taxes and fees

Verified guest reviews
Over 9,520 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
110 of Highlands holiday rentals include Wi-Fi access

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

4.9 Average rating
Highlands stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island 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
- Pocono Mountains Holiday rentals
- Fitness-friendly rentals Highlands
- Waterfront rentals Highlands
- Pet-friendly rentals Highlands
- Hotel rooms Highlands
- Rentals with pools Highlands
- Family-friendly rentals Highlands
- Rentals with a fireplace Highlands
- Rentals with a washing machine and dryer Highlands
- House rentals Highlands
- Rentals with breakfast Highlands
- Rentals with a patio Highlands
- Apartment rentals Highlands
- Rentals with a fire pit Highlands
- Rentals with outdoor seating Orange County
- Rentals with outdoor seating New York
- Rentals with outdoor seating United States
- Times Square
- Madison Square Garden
- New York City Center
- New York University
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- Bronx Zoo
- United Nations Headquarters
- Rockefeller Center
- Brooklyn Bridge
- Citi Field
- Empire State Building
- Grand Central Terminal
- Bryant Park
- Statue of Liberty
- Radio City Music Hall
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art
- Fairfield Beach
- Astoria Park




