Holiday rentals in West Point

Flat in Cornwall-on-Hudson

4.92 out of 5 average rating, 109 reviews

Quaint Apartment in Cornwall on Hudson

Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

4.85 out of 5 average rating, 538 reviews

Loft in Cornwall

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.

4.96 out of 5 average rating, 318 reviews

Guest suite in Chester

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Superhost

Flat in Newburgh

4.86 out of 5 average rating, 189 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

4.93 out of 5 average rating, 282 reviews

Luxury home near West Point

Fully furnished luxury townhouse right outside the gate of West Point, Bear Mountain and commuting distance to NYC. The Unit is SPACIOUS, BRIGHT, OPEN, AIRY with Ample STORAGE, HARDWOOD floors on First level, fully carpeted on 2nd level with Central Air. Master Bedroom-En-Suite, Two Additional Good-Size Bedrooms with Huge Closets and Washer/Dryer On 2nd Floor. Beautiful Tiled Kitchen with SS Appliances: Refrigerator, Dishwasher, Stove. 2 assigned parking spots. Level Backyard.

Apartment in Highland Falls

4.96 out of 5 average rating, 107 reviews

Cozy West Point Hide Away and Cadet’s Get Away

Newly renovated basement space in a very quiet secluded neighborhood with a full kitchen, full size bathroom, Fast WiFi, Smart TV, Separate parking, walking distance to Hudson River, Main Street, Bear Mountain State Park, West Point Military Academy and several adventurous hiking trails. For those who like to shop we are located only 20 minutes to the Woodbury Commons and only a 45 minute drive to NYC. Also Stuart International Airport is only a short drive from here.

4.97 out of 5 average rating, 121 reviews

Cozy House 3 Blocks From West Pt

Welcome to this thoughtfully remodeled Historic 1890s home, just steps away from West Point's Thayer Gate. The house is conveniently situated right by Thayer Gate (3 blocks) where there are shuttles to all events and destinations. Steps away (1 block) from the restaurants on Main street and the West Point visiting center and Museum (3 blocks). 10 Mins to Bear Mountain State Park 15 Mins to Storm King Art Center 20 Mins to Woodbury Commons

4.96 out of 5 average rating, 113 reviews

Guest suite in Cornwall

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

Superhost

Flat in Newburgh

4.92 out of 5 average rating, 173 reviews

Ela - a 1 Bed Escape, Washer/Dryer in Unit

Kick back and relax in this calm, stylish space. Located on the second floor of a historic Newburgh building, this apartment features scenic views from oversized windows, in-unit laundry, LED TV & Fios WiFi, and designer furnishings. Queen bed with Casper mattress. Two flights of stairs required. The neighborhood is quiet, with tree lined streets and historic mansions nearby, just 2 blocks always from the Hudson River waterfront.

4.98 out of 5 average rating, 126 reviews

Loft in Mountainville

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.

4.92 out of 5 average rating, 276 reviews

Guest house in Peekskill

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Farm stay in Fort Montgomery

4.98 out of 5 average rating, 196 reviews

Secluded overlook cottage near West Point

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 minutes from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Come, recline on the new outdoor deck, relax by the fire pit and hike/explore the forest trails right out the front door.

Holiday rentals for every style

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Convenient locations with everyday essentials

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A space that's all yours, with room for everyone

Popular amenities for West Point holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in West Point

Guest suite in Highland Falls

5 out of 5 average rating, 13 reviews

West Point 1 Bedroom River View Apt within Home

MatthewRating, 5 stars7 months ago

This was a great experience and the entire process was smooth and easy. Great communication by the owner and really enjoyed it!

4.91 out of 5 average rating, 120 reviews

Home in New Windsor

View House

JamieRating, 5 stars1 week ago

A fantastic stay: totally private yet with expansive views. Birds galore, June was the perfect time to spot them all. House is gorgeous and unique. Fantastic hosts, stayed here 8 years ago and I very much hope to be back before another 8 years passes. Thank you to Lisa and Nafeeza!

5 out of 5 average rating, 38 reviews

Highland Falls Home - 1/2 Mile to West Point

CharlesRating, 5 stars1 month ago

This house in Highland Falls, NY, was perfect for our visit to West Point Military Academy. The house has very nice front porch and back porch. The living room and dining room are nicely equipped. Kitchen is ready-to-use — including basic spices, olive oil, coffee, and coffee filters. Even some snacks tucked into the cabinets and bottled water in the refrigerator. Similarly, the bathrooms have ample towels and wash clothes, hand soap, body wash, and shampoo. Everything immaculately clean. The house is very well located in the small town — you can easily walk to a couple restaurants, or drive. Everything within 6 or 7 minutes. USMA is just down the road. Karen the host is super-responsive and was very accommodating when we needed to adjust our dates. With our family group this was a really convenient and sociable place to stay for our visit.

Flat in Highland Falls

4.82 out of 5 average rating, 55 reviews

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

MandyRating, 5 stars3 weeks ago

Joe came through for us when a previously booked AirBnB cancelled last minute! We had a special event and were in a bind. We were concerned about fitting everyone in our party (4 adults) - with only one bedroom and two smaller sleeper sofas. Joe was very honest that it might be tight and offered an air mattress just in case. It worked out perfectly! The neighborhood is very close to some great restaurants and if you are staying to attend anything at West Point, it’s super convenient! The place is on the smaller side but perfect for a couple or a family with smaller kids. Would stay there again! Thank you Joe!

5 out of 5 average rating, 3 reviews

Long Dog Inn

PatrickRating, 5 stars5 months ago

We cannot say enough good things about our stay at the Long Dog Inn. The house is perfectly appointed, exceptionally clean and, to our surprise, VERY large. It is much more spacious than it appears in the photos. The luxury linens on the beds are extremely comfortable. Danielle is the perfect host, very communicative and kind. We enjoyed many of her recommendations. We loved the quaint feel of Highland Falls and the close proximity to the Academy. We were accompanied on our stay by friends with 8 guests in total. We visited the Academy each day as well as taking a day trip to NYC. Everyone enjoyed the relaxing time we spent in the Inn. We will ABSOLUTELY be back!

5 out of 5 average rating, 6 reviews

Home in Philipstown

Converted Ice House on Fairytale Estate

AnastasiaRating, 5 stars17 months ago

Perfect place for a weekend getaway from the city! Raquel was extremely responsive and helpful during our stay and the property is very unique and pet friendly.

Flat in Highland Falls

4.8 out of 5 average rating, 134 reviews

Cozy 1-bedroom retreat minutes from West Point!

AlexRating, 5 stars1 month ago

smooth, private, & responsive. would definitely book again if i’m in the area