Guestroom features a roaring fireplace. Luxurious mahogany dresser sits next to wall-mounted television

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Fine Lodging near USMA at West Point NY

CARRIAGE HOUSE ROOMS

Guests of the Caldwell House Bed and Breakfast delight in 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.

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 and teas. Individually wrapped 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.

Storm King

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Storm King

The 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.

Most 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 or, if we are full, in the stately “Great Room” in the Connemara House.

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Queen Size Bed
Jacuzzi Tub
Gas Fireplace
Kitchenette Access (Refrig, Microwave, Keurig, Snacks)

Inviting guestroom features rustic fireplace with elegant bedding on a dark wood bedframe; cheery light flows in from windows

Bathroom has stonewall feature with gold wall color and dark wood vanity with mirror

Bathroom has stonewall feature with gold wall color and white bathtub; displays spa amenities

Trophy Point

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Trophy Point

The 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 of the Carriage House. Morning sunlight gently streams through the windows overlooking the inn’s yard will help invigorate you as you awake.

The 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 loveseat and side chair, 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 shower heads spraying in multiple directions – a real treat!

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

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King Size Bed
Gas Fireplace
Wine Cooler
Kitchenette Access (Refrig, Microwave, Keurig, Snacks)

Inviting guestroom features corner fireplace and hardwood floors and neatly made bed. Wall color is a pleasing velvety heather

Shower in bathroom displays bright white towels, bathrobes and spa amenities

Inviting guestroom features corner fireplace, bright white window curtains and neatly made bed. Wall color is a pleasing velvety heather

Vineyard Room

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Vineyard Room

The 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.”

The 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 shower heads and stately fixtures.

In the morning, a bountiful breakfast is served in the Main House Dining Room or, if we are full, in the stately “Great Room” in the Connemara House.

Book Now Enhance Your Stay

King Size Bed
Gas Fireplace
Kitchenette Access (Refrig, Microwave, Keurig, Snacks)

Pristinely clean bathroom features luxurious dark wood vanity with mirror and spa amenities

Inviting guestroom features a warm fireplace with two charming sitting areas; walls are in soft moss green, floors are hardwood

Inviting guestroom features a warm fireplace with two charming sitting areas; walls are in soft moss green, floors are hardwood

Freedom Road

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Freedom Road

The 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.

The Freedom Road Room is one of the two rooms in the Carriage House 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, 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.

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Queen Size Bed
Jacuzzi Tub
Gas Fireplace
Wine Cooler
Kitchenette Access (Refrig, Microwave, Keurig, Snacks)

Guestroom displays soft green wall colors with hardwood floors and mahogany sleighbed; bedding is florals with cream

Guestroom features a roaring fireplace. Luxurious mahogany dresser sits next to wall-mounted television

Elegant bathroom with cream walls and tile features dark brown wood tones on vanity