House vacation rentals in Highlands

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Top-rated house rentals in Highlands

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Guest favorite

Home in Beacon

4.99 out of 5 average rating, 119 reviews

NEW! Stylish Home in the Heart of Beacon

This Scandinavian style home in the heart of Beacon is bright, airy and modern with beautifully-restored architectural details. Located on a quaint street in the best part of town just steps away from the Roundhouse and Main Street. Enjoy the brewery, bars, restaurants, shops, galleries, and so much more - all within walking distance. Every piece of furniture and decor was handpicked to provide you the perfect designer-quality getaway, focusing on natural simplicity with contemporary luxuries.

Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 109 reviews

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.

Guest favorite

Home in Newburgh

5 out of 5 average rating, 120 reviews

Hillcrest Glasshouse - a minimalist modern retreat

The Hillcrest Glasshouse is a fully renovated peaceful retreat with modern carefully selected furniture featuring a breathtaking view over the Hudson River with a fully equipped kitchen, outdoor fire pit, outdoor grill, indoor fireplace, AC, Sonos sound system, Netflix, Amazon Prime, Cable and excellent Wifi to satisfy all leisure and home office activities. This beautiful getaway is only 70 miles away from midtown NYC and close to many of the Hudson Valley's most visited destinations.

Guest favorite

Home in Warwick

4.89 out of 5 average rating, 126 reviews

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.

Guest favorite

Home in Cold Spring

4.94 out of 5 average rating, 162 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, 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.

Superhost

Home in Peekskill

4.9 out of 5 average rating, 177 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.

Superhost

Home in Cornwall-on-Hudson

4.91 out of 5 average rating, 195 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.

Guest favorite

Home in Wappingers Falls

4.93 out of 5 average rating, 176 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.

Guest favorite

Home in Highland Falls

4.96 out of 5 average rating, 101 reviews

Enjoy Walking Privileges! WestPoint Farmhouse

Walk to USMA West Point! Stay at an Old Grad mom’s beautiful Farmhouse located right outside Thayer Gate and really enjoy walking privileges!Located in gorgeous Hudson River Valley, this luxurious 1500+ sqft home has central AC and a great backyard for entertaining! Coffee Maker, High Speed WiFi, SMARTTV, 350 Roku channels, sports, Netflix and Amazon Prime! Allergen free environment. NO SMOKING or VAPING, PETS! NO EXCEPTIONS OR LOSS OF DEPOSIT.

Guest favorite

Home in Cold Spring

4.89 out of 5 average rating, 190 reviews

The Foundry House by the Hudson River

The Foundry House is an ivy covered historic brick home, built in 1800. It was used as workers quarters for West Point Foundry and its lumberyard during the Civil War until 1911. It has been beautifully restored into a cozy and comfortable home. It’s located on a quiet street a block away from Main Street, half a block away from the Hudson River and the Bandstand, and a minute walk to Cold Spring Metro North Hudson Line Train Station.

Guest favorite

Home in Highland Falls

4.99 out of 5 average rating, 157 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!

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 728 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.