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.

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!

Flexibility in Flight

Two women in yoga pose in light flilled room.

Starting at $255 per couple

Need a new perspective in the New Year? How about turning your life (or at least yourself) upside down? The Caldwell House Bed and Breakfast has teamed up with Flexibility in Flight to offer guests an aerial silks class. While there are some beginner classes, the school will work to accommodate beginners in most of its classes. The antigravity-like experience supports your body without compression of the spine and helps to clear your head. Package costs start at $255 plus tax per couple per night and includes admission for each person to one aerial silks class; weekends require a two-night stay; subject to availability and runs from January to March 2018.

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 through December 31, 2018 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.

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