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Specials & Packages

Make the most of your vacation or romantic weekend getaway in New York’s Hudson Valley with a travel package at Caldwell House Bed and Breakfast.

Our packages and add-ons offer guests a great value in lodging, as well as the opportunity to explore wonderful local activities and attractions, resulting in a memorable and affordable Hudson Valley experience.Check out our current offerings, and be sure to check back often to see more travel specials.[Read More…]

Shop ’til You Drop
Pie on the Pillow
At Ease Active Military Special

Add Ons/Our Store

Massages: $100 per person
Massages are available from our licensed professional Massage Therapists.
Massages must be arranged 48 hours prior to arrival to allow for scheduling; give us a call!

Bicycle Rental: $40 per bike per day
Rent a Bicycle and Enjoy the Hudson Valley on 2 Wheels! Take all the hassle out of lugging your bikes around… just rent bikes from Caldwell House Bed and Breakfast (available at time of reservation)!

Peddle your way down to Storm King Art Center (3.5 miles)…
Or spin your way to the Brotherhood Winery (1.5 miles)
Or ask us for one of the many biking & hiking trail maps we have here at the inn!

Shop ’til You Drop!

Take advantage of our Holiday Season Starter Package to get your holiday shopping off to a great start! We are just minutes from Woodbury Common Premium Outlets where treasures and bargains await. Stay with us now through December 31, 2017 and receive these exclusive goodies:
  • Discount book coupon to save money at area stores
  • A welcome cookie to whet your appetite 
  • A homemade, three-course breakfast 
  • Shopper’s Survival Package (water and snacks)
  • Hot chocolate with marshmallows for warmth and rejuvenation when you return

This festive package starts at $185/room; price varies depending on room selection and length of stay; minimum two-night stay required on weekends.


Pie on the Pillow – Back by Popular Demand!
Last year our guests went absolutely wild over our Pie on the Pillow turn-down service, so guess what?  Dena is in the kitchen, baking those tasty little treats again!

Here’s what she is pitting, slicing & dicing for the fillings:

What will we be serving on your next visit? Be sure to ask when you make you reservation for a stay between September 12th and the end of October!

Take a selfie of you enjoying your pie and post on Facebook or Twitter! #pieonthepillow

At Ease – Active Military Special!
We know the drill and have created a military-inspired package that lines up with West Point’s Eisenhower Hall Theatre’s entertainment schedule and incorporates a meal by a CIA-graduate:

  • Stay 2 nights at the Caldwell House
  • Receive $50 toward a pre-show dinner at Mamie’s Buffet (a cadet restaurant overlooking the Hudson River)
  • Valid 10/1/16 – 4/16/17
  • Paperwork:  must present valid active military ID at check in
  • Call us and use booking code:  At Ease!
  • Packages start at $400 plus tax; theater tickets are purchased separately

Those looking to book the “At Ease” military-inspired getaway will want to plan around the theatre’s schedule. Before you reserve, double-check their website for any scheduling changes.

Eisenhower Theatre Schedule Time Date
Frankie Avalon 3pm Sun. 10/16/16
Billy Gardell 8pm Sat. 10/29/16
The Colonial Nutcracker 3pm Sun. 11/20/16
The Irish Tenors Christmas 3pm Sun. 12/11/16
Cirque Dreams Jungle Fantasy 5pm Sun. 1/29/17
Rhythm of the Dance 3pm Sun. 3/5/17
Scottish Tattoo 8pm Sat. 4/1/17
Annie 5pm Sun. 4/30/17