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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 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…]

New Yeas Eve: Happy and Safe Revelry
If you’re looking to get out of the city and leave your worries behind this New Year’s, consider taking a train to the Caldwell House Bed and Breakfast!

Here are the details on our fabulous New Years Eve package:

  • Early evening “Happy Hour” at the Inn
  • Transportation to a dinner/dance event at Anthony’s Pier Nine where the revelry continues into the wee hours
  • Transportation back to the Inn just before and after 2015
  • Those returning before the clock strikes midnight will receive complimentary champagne and desserts
  • Watch the Ball drop on the inn’s new 75-inch 4KHDTV
  • New Year’s Day brings a delicious breakfast buffet

Packages start at $420 per person, per night, based on double occupancy.
2 night minimum stay required.

Wine Trail Hopper PackageFineries at the Wineries
A day of wine tasting is the perfect way to kick off the holiday season – but you can only enjoy so much if you have to drive. As always, we have all the details covered. Pick up your grapevine wreath and souvenir wine glass at the first of your 14 winery stops. Receive a holiday ornament to add to your wreath at each winery.

What’s Included:

      • 2-night stay for 2 people
      • Private Transportation
      • Wine Tour admission ticket
      • Complimentary Wine Glass
      • Grape Vine Wreath
      • Complimentary Ornaments from each winery visited
      • Complimentary Ornament from The Caldwell House

Dates:  Saturday & Sunday weekends:
Nov 22-23, Dec 6-7, or Dec 13-14, 2014
Tour Times: 10am – 6pm
Wine Trail Hopper Package Prices starting at $600 per couple*
* starting price does not include transportation, transportation costs vary based on the size of your party; contact John & Dena for details.

Wine Trail Hop Package
Here’s a fun package to enjoy between now and the start of the new year:
Package includes:
• Three nights in a guest room.
• S’mores by the inn’s fireplace
• Visit a vineyard of your choice along the historic Shawangunk Wine Trail.
Cost: $575 ($192 per night), double, November 1, 2014 – January 11, 2015

Active & Retired Military …  A Big Patriotic Thank You!
Military personnel are always ready, on all fronts. Now it is time to unwind in the Hudson Valley and enjoy its history and beauty!

      • Book 2 nights: Tuesday & Wednesday & Monday is free!
      • Call us and use the Booking Code:  Military
      • Valid:  August 1 – September 30, 2014
      • Paperwork:  must present valid military identification

School’s Out – Teachers Special!
Caldwell House is proud to join in their ®Travel for Teachers program, offering teachers from across the country to take a break from their busy school-year schedules and enjoy a special discount on us as our thank you for all their efforts!

      • Stay at our historic bed and breakfast for 2 nights (Sun-Wed)
      • Receive a third night free
      • During the months of July & August 2015.
      • Teachers, give us a call and tell us which school you are actively teaching at and book your July or August 2015 visit to Caldwell House!

White Glove Wine Getaway Package
It’s so much fun touring wineries, but after a couple of stops, you might already be feeling the tastings you have just sampled.  Leave the car keys with us, grab a few of your friends, and book this exclusive White Glove Wine Getaway we have put together in conjunction with the Pasta Primo Vino event taking place April, 2015.

White Glove Wine Getaway Details for Groups of 8-10 People, Pricing Includes:

      • 2-night stay
      • 2-day wine tour & tasting
      • Limo Pick Up at our door
      • Cooler packed with water & light snacks to keep you going
      • Wine Tour Tickets

Package Price:  $879 per couple plus tax
Optional 1 day wine tour and all of the above:  $759 per couple plus tax

If you have a larger group, call John or Dena for pricing details at 845-496-2954.
This is going to be a popular package so call and book soon!

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/li>
      • 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


Bicycle Rental
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!

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!

Bike Rental Fee: $40 per bike per day (available at time of reservation)