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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…]

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!

Pie-on-the-Pillow 2015

This fall, we will be gathering farm-fresh produce from Blooming Hill Farm, Grove, Soon Orchard, Roe’s Orchard, and Jones Farm … you can only imagine the pie making schedule we have on the books!

We have put together a two-month ‘Pie on Pillow’ Calendar for September/October 2015 – but guests who call ahead may request their favorite pie for pre-slumber bliss!

2015 Pie Calendar (by week)

August 31 Blueberry Pie
September 7 Blueberry Crumble Pie
September 14 Blueberry Peach Pie
September 21 Peach Pie
September 28 Nectarine Pie
October 5 Pear Pie
October 12 Pecan Pie
October 19 Apple Pie
October 26 Apple Crumb Pie

*Mini pies subject to change based on availability/seasonality of ingredients


Beer & Breakfast (Beercation!)
Sit back and grab a cold one as we launch our first “Beer & Breakfast beercation” package along the Hudson Valley Beer Trail in partnership with the Little Beer Bus Hudson Valley Brewery and Distillery Tours. even picked up this fun package!

The Beer & Breakfast beercation package is available for couples and groups. The package includes:

Pick-up and drop off at the Inn one day of your stay in a bus, limousine, town car or SUV depending on group size. Transportation to your choice of three Hudson Valley breweries along the Hudson Valley Beer Trail. If you’re uncertain The Little Beer Bus will help you choose. (Available options include: 2 Way Brewing Company, Blue Collar Brewery, Hyde Park Brewing Co., Keegan Ales, Newburgh Brewing, Peekskill Brewery, Tuthilltown Spirits, and the Warwick Valley Distillery).

  • 5-6 generous beer tastings/beer garden(s) at each brewery
  • A grand brewery tour with a beer in hand and quality time with knowledgeable brewmasters
  • Full lunch, snacks, bottles of water, raffle prize, time to relax and have fun in the breweries and/or outdoor beer gardens
  • Tour guide that will meet you at each brewery for a fun-filled day
  • 2-night stay at the Caldwell House Bed and Breakfast
  • Complimentary three course gourmet breakfasts
  • Complimentary WiFi

Package starts at $800 per couple plus tax. One-night packages are sometimes available at a reduced rate based on time of year and availability.

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 9/11/15 – 4/17/16
  • 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 Hall Theater Schedule Time Date
Bill Engvall “Here’s Your Sign” 8pm Sat. 9/12/15
42nd Street 3pm Sun. 10/11/15
Paul Anka 3pm Sun. 11/1/15
The Coasters 3pm Sun. 11/15/15
Cirque Dreams Holidaze 5pm Sun. 11/22/15
The Toy Shoppe (staring Alan Thicke) 3pm Sun. 12/13/15
Adam Trent – The Futurist 8pm Sat. 1/23/16
Disney’s Beauty and the Beast 5pm Sun. 2/28/16
Women of Ireland 8pm Sat. 3/5/16
Live from Nashville 8pm Sat. 4/2/16
Mamma Mia! 3pm Sun. 4/17/16


Inn to Inn Cycle & Leaf Peeping Package
Spin your wheels through crunch leaves from one charming inn to another across the Hudson Valley in peak leaf-peeping season. Drive or take Metro-North (1-hour North from NYC on Port Jervis line to Salisbury Mills/Cornwall) to arrive at the first of two inns: the Caldwell House Bed and Breakfast; complimentary transportation from the train to the inn on request. Enjoy a hearty homemade breakfast the next morning and grab complimentary water bottles for a proper send off. Bike about 21 miles (33 kilometers) through quiet country roads, winding trails, scenic country landscapes to reach the Pine Bush House Bed and Breakfast in beautiful Pine Bush, NY, where you’ll be welcomed with apple cider.
Next day, another homemade breakfast starts your return journey to the Caldwell House.

What’s included:

  • One night mid-week stay at the Caldwell House Bed and Breakfast
  • One night mid-week stay at the Pine Bush House Bed and Breakfast
  • Homemade breakfast each morning
  • Water bottles to take on cycling trip
  • Suggested cycling route
  • Luggage transportation from inn-to-inn
  • Welcome beverage upon arriving at inn after cycling
  • Complimentary WiFi and amenities
  • Complimentary parking, for those driving to starting inn

Package Price:  $400 + tax based on double occupancy
Available: Sundays through Wednesdays
September 7th through November 5th 2014
Blackout dates: October 12-14, 2014
Bicycle rental available for additional $40/day per bike.
To reserve this package call the starting inn, Caldwell House, at 1-800-210-5565