House vacation rentals in Highland Falls

Find and book unique houses on Airbnb

Top-rated house rentals in Highland Falls

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Guest favorite

Home in Philipstown

4.92 out of 5 average rating, 110 reviews

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, Fahnestock State Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $75 per stay. I live close by so I’m available for help or assistance during your stay.

Jul 20 – 27

G$57,943 GYD per night

Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

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, crib and baby monitor, 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.

Oct 31 – Nov 7

G$115,125 GYD per night

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 278 reviews

This New House

Unique custom built new home constructed purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dinning area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and floors. You will also see plenty of natural pine, hickory, and local cedar throughout the house.

Apr 15 – 22

G$30,136 GYD per night

Guest favorite

Home in Putnam Valley

4.96 out of 5 average rating, 102 reviews

Lake Cottage Near Sleepy Hollow, Westpoint & NYC

Escape to this private lakeside cottage. Just 1h drive from NYC near lots of skiing: 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 The cottage can accommodate up to 10 guests and is family-friendly. Pets are welcome! WiFi is extremely fast and we have free electric car charging.

Jul 29 – Aug 5

G$149,129 GYD per night

Guest favorite

Home in Cornwall-on-Hudson

4.95 out of 5 average rating, 104 reviews

Charming Hudson Valley Home: Minutes to West Point

**Currently booking for West Point Graduation 2025. 5-night minimum** Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available

May 31 – Jun 7

G$95,741 GYD per night

Guest favorite

Place to stay in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1200 sq. Ft. Suite staycation, located in a beautiful, safe, quiet cul-de-sac neighborhood. Modern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with YouTube TV/Amazon Prime/Netflix, Apple iPhone charger, 2000mb Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking or vaping inside and outside the premises. No children or infants

Mar 9 – 16

G$34,022 GYD per night

Superhost

Home in Cornwall-on-Hudson

4.92 out of 5 average rating, 131 reviews

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

Nov 18 – 25

G$105,761 GYD per night

Guest favorite

Home in Cornwall-on-Hudson

4.94 out of 5 average rating, 176 reviews

Waterfall @ 1850 Cottage near West Point/StormKing

Check us out on IG @upstategetaways Nestled in the Hudson Highlands, The Storm King Mountain House sits on a secluded 4 acres with a huge patio deck and a path into the Storm King Mountain Trailhead. The house is right next to West Point, Cornwall-on-Hudson, the Hudson River, and centered between the Hudson Highlands and Black Rock Forest. Our house is perfect for any weekend getaway or a vacation with family and friends. We are a quick 1-hour drive from New York City.

Oct 31 – Nov 7

G$105,145 GYD per night

Superhost

Home in Peekskill

4.9 out of 5 average rating, 154 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 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.

Dec 31 – Jan 7

G$79,322 GYD per night

Guest favorite

Home in Wappingers Falls

4.97 out of 5 average rating, 107 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. 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.

Jul 9 – 14

G$34,072 GYD per night

Guest favorite

Home in Newburgh

5.0 out of 5 average rating, 124 reviews

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

Nov 23 – 30

G$71,358 GYD per night

Guest favorite

Home in Highland Falls

4.99 out of 5 average rating, 142 reviews

Spacious, bright 5 bedroom house near West Point

Newly renovated 5 bedroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

Oct 26 – Nov 2

G$97,268 GYD per night