Fine Lodging near USMA at West Point NY


Guests of the Caldwell House Bed and Breakfast delight in the both the luxury and history of The Carriage House and its four guest suites, each contributing to our award-winning, Select Registry and Diamond Collection status.[Read More…]

The Carriage House, built in the early 1800s to house the Caldwell Family carriages, has been completely refurbished. We succeeded in being able to keep the original structure intact – including preserving the beams and stonework – while making it a romantic and rustic – yet state of the art – home for our guests to relax in luxury. A pleasing alternative to hotels when visiting West Point and the Hudson River Valley, each Carriage House room contains all the same common features that our Main House Rooms have, and then some!

There is full access to the Carriage House common area’s kitchenette, which comes complete with a large refrigerator, microwave, Keurig, specialty coffees, teas, and soft drinks. Fresh snacks are in plenty supply and are available around the clock.

Relax with a glass of wine or a cup of coffee on the Carriage House porch, play a board game in the common area, or stroll over to the Main House to enjoy any of the common rooms with fellow guests.

side-carriage-3The Storm King Room, named for the nearby Storm King Art Center – 500-acres of landscaped fields, hills, and woodlands recognized as one of the world’s greatest outdoor sculpture gardens – is located on the ground floor level of the Carriage House. Its rustic, yet romantic feel has quickly turned the room into a guest favorite.[Read More…]

side-carriage-6Most of the original wood and stonework (circa 1803) remains in place – giving the room a feel of a bygone era. An impressive queen-size bed, top-of-the-line mattress, and luxurious bedding will guarantee a blissful sleep. The room has a lingerie chest, a cherry wood framed floor mirror, comfy love seat and a beautiful antique chair as there is ample space for seating throughout the room, and plenty of space to snuggle up in front of the fireplace.

Storm King’s spacious bathroom comes complete with a Jacuzzi tub for two, a separate shower, and beautifully appointed fixtures.

In the morning, breakfast awaits in the B&B’s Main Dining Room.

side-carriage-2The Trophy Point Room, named for West Point’s famous Battle Monument site (one of the largest columns of granite in the world), is located on the front side of the second floor. Morning sunlight, gently streams through the windows overlooking the inn’s yard, will help invigorate you as you awake.[Read More…]

side-carriage-7The handsome king-sized bed, super comfy mattress, and top-of-the-line bedding will assure you a dreamy night’s sleep. The room also comes with a Queen Anne’s chair and love seat, affording you much space to read, work, or enjoy a fire. An antique chest of drawers provides you plenty of space to lay out your belongings. The large en-suite private bathroom comes with a supersized shower with showerheads spraying in multiple directions – a real treat!

Once you are “up and at ‘em”, march on over to the Main House Dining Room for the best breakfast you’ve had in a while! Then it is off to conquer the lovely Hudson Valley.

side-carriage-1The Vineyard Room,named for local wineries such as Brotherhood (America’s Oldest Winery), Palaia Vineyards, and others on the Shawangunk Wine Trail, is located in the north-facing side of the second floor providing our guests with a “peaceful, easy feeling.”[Read More…]

side-carriage-8The striking king-sized bed, super comfy mattress, and luxurious top-of-the-line bedding will assure you a restful night’s sleep. In addition, cuddle up on the large and comfortable chaise sofa or read a book by the fireplace in the lovely Queen Anne’s chair. The room has a closet for your personal use and the large, private en-suite bathroom has a huge shower with multiple showerheads and stately fixtures.

In the morning, a bountiful breakfast is served in the Main House Dining Room.

side-carriage-4The Freedom Road Room is named after the nearby “Freedom Road Trail” – the road leading from the last encampment made by General Washington’s army before the end of the Revolutionary War. Nearly two centuries later, the 52 American hostages traveled this same route from Stewart Airport to West Point after their release from captivity in Iran. Americans were able to celebrate their freedom along this road in both the 18th and 20th centuries.[Read More…]

side-carriage-5The Freedom Road Room is one of the two rooms on the ground floor level and comes with its own private entrance from the outside and a beautiful queen-sized sleigh bed. Additional features include a private closet, lingerie chest, a desk to work on, and a comfortable swivel “chair and a half.”

Freedom Road’s private en-suite bathroom features a Jacuzzi tub, separate shower, and beautiful fixtures.

In the morning, march on over to the Main House Dining Room and join our other guests for a breakfast to remember with enough food to feed an army!