Caldwell House Bed and Breakfast

Select Registry Member Since 2014

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Caldwell House Bed and Breakfast

Select Registry Member Since 2014

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The Basics

The Caldwell House Bed and Breakfast is an award-winning romantic destination located in the Lower Hudson Valley. We are located just an hour outside of New York City. Enjoy hiking, art, history, wineries, and, most important, relaxation when you stay with us! Enjoy a gourmet breakfast each day, along with plenty of snacks that are provided in your room. We hope to see you soon!

Things We Love


We are just two miles away from the nation's oldest winery, Brotherhood Winery

Hiker in boots on a trail

We have many nearby scenic hiking trails


Awake each morning to a full three-course homemade breakfast in one of our two formal dining rooms

At A Glance

  • Complimentary WiFi
  • Free On-site Parking
  • Adult Only
  • Green/Environmentally Friendly
  • Fireplaces in Some Guestrooms
  • Private Entrances - Some Rooms
  • Jetted Tubs - Some Rooms
  • Full House Rental Available

Best For

  • Outdoor Activities
  • Romantic Retreat/Honeymoon Destination
  • Wine/Vineyard Destination

In The Know

Here are a few things you can't miss when you visit...

  • The National Purple Heart Hall of Honor offers visitors an incredible journey through military history as well as reminders of human sacrifice and the cost of freedom
  • Visit Brotherhood Winery, it is the oldest winery in the country
  • Fourth of July at West Point Military Academy is not to be missed
  • Visit the Museum Village -The largest living history museum in New York State


This New York inn, built while Thomas Jefferson was President and opened the same year as the USMA at West Point, offers the architectural splendor of that era while tastefully and discretely incorporating all the modern conveniences that today's traveler seeks. We have expanded to include 2 new buildings - the former Caldwell House Bed and Breakfast and the Caldwell Barn. Each as been lovingly restored. We've attempted to save as much of the original look and feel while, at the same time, incorporating modern amenities and technology.

Our guests will find the original wide planked wooden floors, high ceilings with their crown molding, large, beautifully designed fireplaces that the first owners of the home used and enjoyed. Over the years, the Inn has been meticulously cared for and updated to add all the comforts of a modern home without doing anything to harm its original charm.

Each room has an en-suite bathroom - all with showers and several with oversized Jacuzzi tubs. Large "Smart" HDTVs, strong Wi-Fi signal, extremely comfortable King and Queen sized beds, in-room Climate Control settings, and luxury amenities welcome each guest. Watch a Netflix or Hulu+ movie or enjoy a delicious bottle of wine in front of a fireplace that many of the rooms have. Sit on the original wrap around front porch or take a stroll across the street to watch the Moodna Creek wander its way toward the Hudson River. Stroll the grounds in the warm weather months and "smell the roses.”

After a blissful night's sleep, awake to the smell of Dena's delicious three-course breakfast. The menu changes daily and all special requests are honored (just give us advanced notice so we have the freshest of ingredients on hand).

Our multi-award winning Bed and Breakfast awaits you and its owners, Dena and John, look forward to providing you with a stay you will remember for a long time to come.


Inn Amenities: Free Onsite Parking, Gardens on Property, LGBT Friendly, Green Environmentally Friendly, Limited Spa Service, Dedicated Spa Service, Concierge Services

Food & Wine

At Caldwell House Bed and Breakfast, breakfast is a celebration of the beginning of the day. Enjoy a wonderful start to your day with Dena's sumptuous three large, delicious courses. Sip some delicious coffee, tea, or juice while chatting with our friendly and interesting guests.
The sun drenched Dining Room with its historic cranberry walls and flowered curtains is furnished with a large formal table and chairs. A lovely mahogany china cabinet enhances the appearance of the room. When the Inn is fully booked, we set up separate, smaller table settings for those seeking a more intimate setting.
*** Due to the pandemic we are currently providing the breakfast delivered to the room in a basket. We have several spots around the property where you can enjoy your breakfast.
Dietary restrictions (e.g. Vegan, Vegetarian, Gluten Free, Lactose intolerant, etc.), with prior notification, are happily honored.
Whenever possible, we shop at our local Orange County farms thus bringing you a real “farm to table” experience. Each day’s meal will leave you looking forward to mornings to come!

Meals Offered: Breakfast

Restaurant on Premises: No

Special Diets Accommodated: Vegetarian, Vegan, Gluten Free, Yes

Breakfast: Complimentary

Breakfast Service: Full

Breakfast Seating: Communal, Set Times

Pub/Tavern on Premises: No

Dining Amenities: Complimentary Beverages, Complimentary Snacks, Complimentary Early Coffee Tea

Rooms & Suites

The Caldwell House Bed and Breakfast has 14 luxurious rooms located in 3 buildings on 8 landscaped acres. Please see our website to see pictures and videos of each of the rooms on the property.

Accommodations: Suites

# of Rooms: 14

Beds: Queen, King

Room Entertainment: Cable TV

Handicap Accessible: Limited

Room Amenities: Air Conditioning, Alarm Clocks, Antique Furnishing, Bathrobes, Fireplace, Hair Dryer, Ironing Boards, Microwaves, Private Deck, Private Entrance, Refrigerator, Rollaway Available, Telephones, Whirlpool or Jacuzzi

Guest Services

Several of our rooms are ADA compliant.

Internet Service: Wireless, Complimentary

Front Desk/Security: OnSite, Business Hours

Corporate Rates: No

Inn Amenities: Free Onsite Parking, Gardens on Property, LGBT Friendly, Green Environmentally Friendly, Limited Spa Service, Dedicated Spa Service, Concierge Services

Location Type

Location Type: Small Town/Village, Rural


Due to the current pandemic, we are now delivering a breakfast (hot breakfast) basket to the room. We have several spots around the property for you to eat if you would like to eat outside of your room. We thank you for your understanding during this time.

Minimum Stay Required: Weekends, Holidays, Peak Season

Pet-Friendly: No

Smoking Policy: Outside Only

Family Friendly: No

exterior inn

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