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.

Wonderful Winter Savings

White snow-covered ground, green pine trees and faintly shining sunlight

Save up to $25

Now is the perfect time to take a cozy winter getaway in the Hudson Valley. Save up to $25 on select rooms now through the end of March. (Savings have already been applied to room rates in our reservation system)

Click here to book now!

Individual or Couples Messages

Women laying face down on table with white towel drapped over getting a message.

$100 per person

Our licensed Massage Therapists will massage your cares away in our wonderful Spa Area.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!

Shop 'til You Drop!

woman holding shopping bags in her hands

Starting at $175/room

Take advantage of our Starter Package to get your shopping off to a great start! We are just minutes from Woodbury Common Premium Outlets where treasures and bargains await. Stay with us now and receive these exclusive goodies:
Discount book coupon to save money at area stores;
A homemade, three-course breakfast; and
Shopper’s Survival Package (water and snacks)
This festive package starts at $175/room; price varies depending on room selection and length of stay; minimum two-night stay required on weekends. Call (845) 496-2954 to book.

Pie on the Pillow - - Back by Popular Demand for the month of September!

Two green pottery coffee mugs with Caldwell House emblem and two petite individual size apple pies.


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: Cherry, Apple, Fudge, Pecans or Pumpkin

What will we be serving on your next visit? Be sure to ask when you make your reservation for a stay between September 5th and September 30th!

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