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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.

It’s All Academic
Getting ready to visit college campuses with your teenager and thinking you’ll have to scrap that summer vacation?  Nope!

You can combine your getaway with a campus tour – and we’ll even give you extra credit: we’ll provide a third night’s stay for free when you book two nights Sunday through Wednesday.
Valid:  April – August, 2015, excluding Holidays.

Of all the colleges in the Hudson Valley, we are located closest to the United States Military Academy at West Point.

Other colleges you might be visiting with your candidate:
Adelphi’s Hudson Valley Center, Culinary Institute of America, The, Dutchess Community College, Iona College, Marist College, Mount St. Mary’s College, Siena College (the owner’s alma mater), Sullivan County Community College, SUNY New Paltz, SUNY Orange (Middletown), SUNY Orange (Newburgh), SUNY Purchase, SUNY Rockland Community College, Ulster County Community College, Vassar College, and more.
Give us a call and book your stay with us!

White Glove Wine Getaway Package (Pasta Primo Vino Event)
The Caldwell House Bed and Breakfast is offering guests the chance to drink and dine responsibly this Spring with its White Glove Wine Getaway. Guests traveling in the area for the annual Shawangunk Wine Trail Pasta Primo Vino event may sip and savor regional wines and pasta dishes at up to 14 wineries and leave the driving to their designated chauffeur.
Pasta Primo Vino takes place April 11-12, 2015.

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

          • 2-night stay
          • 2-day admission to Shawangunk Wine Trail Pasta Primo Vino event
          • Limo Pick Up at our door
          • Limo fully stocked with revitalizing refreshments
          • Designated Limo Driver

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!

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!

What’s Included:

          • 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

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, 2015
          • Paperwork: must present valid military identification

Farm to Fork Country Feast:
Event Date: June 26, 2015 (watch for a future Farm to Fork event!)

We will be sourcing the freshest, most hyper-local, ingredients for our very first farm-to-fork country feast on Friday, June 26, 2015!

The evening festivities begin at 6 pm with a cash bar and light hors d’oeuvres.
Dinner will be served from 7-10 pm and will include two glasses of local wine: Palaia’s Cabernet Franc and/or Riesling from Brotherhood Winery.

Live entertainment will be provided by The Parting Glass Band, a local musical group with Irish roots. The Fresh Café will cater this event using ingredients from the following regional farms and purveyors: Jones Farm in Cornwall, Gray Family Farm in New Windsor, Blooming Hill Farm in Blooming Grove, Brotherhood Winery in Washingtonville, Palaia Vineyards in Highland Mills, and Lowlands Farm in Warwick.

Included in your local Farm to Fork Country Feast:

              • Five-course tasting menu
              • Menu details will be released one week prior to the event to ensure only the freshest local ingredients are used for inspiration. We are leaning toward grilled asparagus, baby kale and pancetta crostini with roasted spring onion vinaigrette, pan seared striped bass, spring vegetable risotto cake, carrot puree, and many other dishes prepared specifically for the event.
              • Tables will be set up in the inn’s new ‘Great Room’ with additional seating outside for those wishing to dine al fresco under the stars.
              • The cost to attend is $150 per person.
              • Call to book your seat at the table!

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

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

Knit Me, I’m Irish
Grab your knitting needles! The Caldwell House Bed and Breakfast and the Cornwall Yarn Shop are marking St. Patrick’s Day by offering guests a chance to knit their very own Irish scarf using Irish yarn at the historic Irish inn on Mondays in March.

The Irish scarf knitting classes will be held here at the Inn based on availability these dates:

Mondays March 2, March 9, March 16 and March 23rd 2015 from 2-4 pm
Monday, March 30th 2015 from 7-9 pm.

The hands-on experience is available to guests through the “Knit Me I’m Irish package” but the class itself is open to the public independently with a $40 fee plus tax, which includes supplies. Knitters may return on a following week for a recurring fee.

Knit Me, I’m Irish package includes:

          • 3-night stay at the Caldwell House Bed and Breakfast for the price of a 2-night stay (1 night free!)
          • Admission and all supplies for two to the Irish scarf knitting class
          • Complimentary three course gourmet breakfasts
          • Free WiFi at the inn so you can show off your new creations
          • If your partner isn’t interested in knitting, they could always join others who will be watching the basketball tournament games on the 75” 4KHDTV

Package starts at $530 per couple plus tax; the Knit Me I’m Irish package is available Sunday – Tuesdays in March 2015.