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 building - the former Caldwell Carriage House 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.
Select Registry member since 2014
- Minimum Stay Required: Weekends, Holidays, Peak Season
- Pet Friendly: No
- Smoking Policy: Outside Only
- Family Friendly: Over 12
- Inn Amenities Refine Search: Fitness Center, Shuttle Service, Free Onsite Parking, Gardens on Property, Wine/Spirits available
Food & Wine
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.
Dietary restrictions (e.g. Vegan, Vegetarian, Gluten Free, Lactose intolerant, etc.), with prior notification, are happily honored. A menu of the day is provided out with the first names of the guests, the weather, and "This Day in History."
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
- Breakfast: Complimentary
- Breakfast Seating: Individual Tables, Communal, Set Times
- Breakfast Service: Full
- Complimentary Breakfast: Yes
- Offered Amenities: Complimentary Beverages, Complimentary Afternoon Tea/Refreshments, Complimentary Snacks, Complimentary Early Coffee/Tea, Evening Cocktails, Picnics Available
- Alcohol Permits: Beer, Wine, Spirits
- Special Diets Accommodated: Yes
- Pub/Tavern on Premises: Limited to overnight guests
Rooms & Suites
Guests are invited to choose from rooms in the Main House of the Inn or in the newly renovated Carriage House.
THE MAIN HOUSE
The Harmony Hill Room
· The Catherine Caldwell Room
· The Antrim Room
· The Moodna Room
· The Butter Hill Room
· The Trestle Room
Guestrooms in the main house have lovely, original, wide-pine floors dating back to 1803, original door hardware and locks, modern security features, private en-suite baths (two with large 2 person Jacuzzi tubs), King or Queen size beds, luxurious quilted bedspreads, and in-room climate controls. Each room has a large flat screen “Smart” HDTV, with Netflix, Hulu, etc. Wi-Fi service are available throughout the house and property, and an iPad and iHome are available for personal use in each room. Two rooms have private fireplaces while the remaining four have beautiful electric fireplaces. Relax on the stately wrap-around front porch or stroll across the street to sit along the Moodna Creek.
THE CARRIAGE HOUSE
· The Freedom Road Room
· The Storm King Room
· The Trophy Point Room
· The Vineyard Room
The four guestrooms in the Carriage House have wood floors, exposed original wood beams (circa 1803) and either King or Queen sized beds, quilted bedspreads, ample sitting areas, individual room climate control settings, large flat screen “Smart” HDTV’s with Netflix and Hulu+, and free Wi-Fi throughout the house. Each room has a gas fireplace; two have large Jacuzzi tubs for 2 while the other two rooms have oversized showers with multiple shower heads. The Carriage House also has its own Parlor and kitchenette for guest use. Relax on the inviting front porch or on the Freedom Road room’s private patio. Guests in the Carriage House have full access to all the Main House's common areas.
THE CONNEMARA HOUSE
· The Fields of Athenry Room
· The Cliffs of Mohers Room
· The Galway Bay Room
· The Rock of Cashel Room
The Connemara House is built around the original Caldwell House Barn. We named it for the part of Ireland that the Finneran Family came from - an area that is described as a place of contrast, colors, wilderness and warm welcomes. We hope you'll find your stay with us to meet that description.
The four guestrooms in the Connemara House have wood floors, King sized beds, quilted bedspreads, ample sitting areas, individual room climate control settings, large flat screen “Smart” HDTV’s with Netflix and Hulu+, and free Wi-Fi throughout the house. Each room has a gas fireplace; two have large Jacuzzi tubs for 2 while the other two rooms have large soaker tubs. Each room has a private bathroom which includes a large rain showers with body sprays. Each room at the Connemara House has its own private entrance and comes complete with its own Kuerig coffee/tea maker, refrigerator, iPad, and many luxurious amenities. Each room has an inviting front porch with Adirondack rocking chairs.
The Connemara House also contains a large Great Room which is available to guests for small to mid sized weddings, corporate retreats, and other social functions. It comes equipped with seating for 60+, a bar area, and a 75 inch "4K HDTV". Finally, there is a spa area available to all guests for massages and other spa related activities.
- Accommodations: Suites
- # Rooms: 14
- Beds: Queen, King
- Room Amenities: Air Conditioning, Antique Furnishings, Bathrobes, Fireplaces, Hair dryers, Private Deck, Private Entrance, Refrigerators, Rollaway Available, Telephones, Whirlpool or Jacuzzi, Alarm Clocks, Ironing Boards, Microwaves
- Entertainment: Cable TV , CD Players, DVD/Blu-Ray Players, iPod Docking Stations, Music Library, Video Library
- Handicap Accessible: Limited
Several of our rooms are ADA compliant.
- Internet Services: Wired, Wireless, Complimentary
- Corporate Rates: No
- Front Desk/Security: Onsite
- Inn Amenities: Shuttle Service, Free Onsite Parking, Gardens on Property, Business Center, GLBT Friendly, Green/Enviromentally Friendly, Limited Spa Services, Dedicated Spa Facilities, Pub/tavern on Site, Wine/Spirits available, Concierge Services
- Location Type: Suburban, Rural, Mountains, Waterview, Small Town/Village
Weddings & Events
There are several areas on the property where weddings and/or receptions can be held.
Whether it be a small, intimate Elopement, a Vow Renewal, Rehearsal Dinner, or large outdoor Tented Wedding the Caldwell House is a perfect choice. Our seven landscaped acres offer many beautiful spots for ceremonies of all types and sizes. Our Event Planning staff will work closely with you to ensure that your experience is the best possible. Contact firstname.lastname@example.org with any questions.
- Events Supported: Private Parties, Ceremony, Receptions, Rehearsal Dinner, Bridal Luncheon, Elopement
- Wedding Services & Amenities: Wedding Planner, Officiant, Caterer, Florist, Photographer, Decorator
- Wedding/Reception/Event Facilities: Indoor, Outdoor
Business Travel & Events
With the opening of the new Connemara House, the Caldwell House is now able to offer several different meeting / event settings. During warm weather months, the options are endless as there are many spots on our 7 acres that offer beautiful sites for open air and/or tented events.
The Main B&B House can accommodate meetings of up to 20 while the new Connemara House boasts a Great Room that will accommodate up to 75. The new event room will include all the amenities successful meeting/events calls for – e.g. high speed Wi-Fi, overhead Projections, telecom, sound systems, etc.
Whether it is the local Chamber of Commerce, Trade Associations, Company meetings/retreats, or just large groups looking for a place to gather and mingle, the Caldwell House has served many happy events. With the addition of the new facilities, we will be able to meet the needs of nearly any group!
- Banquet Seating: Flexible
- Reception Seating: Flexible
- Max Capacity Outdoor: 100+
- Business Travel & Events Max Capacity: 20, 75
- Total Rooms Sq Footage: 300; 1,000
- Total Meeting Rooms: 3
- Meeting Facilities: Indoor, Outdoor
- Meeting Amenities: Onsite Catering
- Meeting Types: Business Meeting, Retreats, Social