Home > New York B&Bs > Greenport Bed and Breakfast Inns > Stirling House Bed & Breakfast

104 Bay Avenue, Greenport, NY 11944, USA    
(800) 551-0654, (631) 477-0654


  1. Relax on the Waterfront Porch. No other inn compares to this ...
  2. Greenport, Long Island Wine Country's central town...
  3. The Shelter Island Room. Beautiful Queen room. The only thing it overlooks is th...
  4. The Shelter Island Room . The bay breezes are amazing. Air conditioning is avail...
  5. The French Room Suite shows life at a different angle...
  6. Take me to Paris! Now you can...without having to get that passport picture take...
  7. The Greenport Room: Majestic, classy, unique...
  8. Stirling House is the ONLY legally wine licensed B&B in LI Wine Country. NOTE: L...
  9. Every day promises a different view. This one did cost extra!...
  10. Facing Greenport Harbor on a small hill stands The Stirling House, built in 1880...
  11. Water's Crest Winery conducting an exclusive wine tasting on the waterfront porc...
  12. The flowers that bloom in the Spring...they just keep on blooming!...

- $495

Book a Room $275 - $495

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5 based on 3 reviews
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Circa 1880. Located in the heart of the village in the historic district, this water-view bed and breakfast offers old-world southern charm combined with modern luxuries. Attention to detail is given all year round. Unwind on the wraparound porch with changing views of Shelter Island. Explore quaint shops, museums and art galleries, all a few steps from the resort. Richly appointed guest bedrooms are inviting and pampering retreats. Dine on bold, contemporary cuisine at one of the award-winning area restaurants. Discover world-class Long Island Wine Country vineyards on a tasting tour or take to the water on an exclusive lighthouse cruise.

For more information visit the website.


$275 to $495

Off Season: $199 to $395

Payment Types Accepted Include Visa, American Express, Master Card, Discover and Cash.

    • Wine
    • Breakfast
    • Snacks/Refreshments
    • Afternoon Tea
    • The Only B&b On The North Fork Of Long Island Licensed By The State Of New York To Serve
    • Sell Wine. Wine
    • Cheese Are Now Served As Alternating Weekend Snack
    • On Request


This property has 3 total guest accommodations with private bath, 3 with fireplaces, 1 with whirlpool, 1 total suite, including 2 two-bedroom suites. The types of beds available include King and Queen.

  • Air Conditioning
  • Bath Amenities
  • Bathrobes
  • Cable TV
  • Computers
  • DVD
  • Fax
  • Fireplace
  • Free parking on premise
  • Gift Shop
  • Hair Dryer
  • Heating
  • Iron/Ironing Board
  • Refrigerator
  • Television
  • Wireless Internet Access

Business Traveler Amenities

  • Hair Dryer
  • Gym Nearby
  • FAX On-site
  • Daily Newspapers
  • Internet Access
  • Iron/Ironing Board
  • Modem Connection
  • Television
  • Wireless Internet Access

Events Hosted

    • Family Reunions
    • Romantic Getaways
    • Honeymoons
    • Weddings
    • Vine Timne All-inclusive Food
    • Wine Getaways
    • Vine University All Inclusive Wine Making Course
    • Game Night
    • Murder Mysteries Wine Tastings
    • Bread Making Seminars

Foreign Languages Spoken




Spa Services

On-Site Spa Services

  • Massages

Inns Of Interest

    • Oldest Continuously Operated Inns
    • Lighthouses

Reservation/Cancellation Policies:

Minimum Stay Requirements

Two-night minimum stay between Memorial Day through October


Full refund if cancellation is with fourteen days notice. Forfeit 50% with less than fourteen days notice unless we can re-rent the room (or 100% on 1 night stays). Less than 72 hours forfeits the total amount (again - unless we can re-rent the room)


4 to 6 p.m. / 11 a.m.

Other Activities

    • Tennis
    • Skiing Cross Country
    • Shopping (Local Crafts)
    • Parks
    • Museums
    • Live Theater
    • Horseback Riding
    • Hiking
    • Golf
    • Fishing
    • Canoeing/Kayaking
    • Bicycling
    • Beaches
    • Art Galleries
    • Antiquing
    • Water Sports
    • Wineries

Historic Interest

Historic Memberships:

  • Local Historical Society

Other Awards:

Award of Excellence 2010, 2011, 2012

Stirling House Baked Pear

This one recipe makes me proud as it makes converts of non pear lovers. I know...I was one of them. My mom liked to bake fruit, and drizzle cognac over a pear or apple as a nice dessert. I thought tweaking this a bit would be a nice addition to the break

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Wonderful Stay!

Thank you for a wonderful stay at your inn. The food, the view, the conversation, your warmth and hospitality made for a relaxed, refreshing weekend. A breath of fresh air in an otherwise too hectic life style. Again, thank you.
Ann I

My ratings for this property      
BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (2 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.


Fantastic Stirling Hourse I first stayed here on 4th of July in 2008 and instantly fell in love with the Stirling House! Clay (owner) is wonderful and treats you like family. His attention to detail is impecable and his breakfasts are out of this world! My friends and I loved our stay sooo much we booked for 2 months later and rhen for a year later!! So here I am a year later and it's amazing! Couldn't wait to be here! I tell all my clients, friends, and family about the Stirling House! It's the best VACATION I have ever been on! This will be a yearly trip (and it's only an hour away from house!). Jennifer ;-)
Jennifer Schey

My ratings for this property      
BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (2 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

The Romantic place to stay

We are regulars at The Stirling House. It is on. Te water, and in the beautiful Village of Greenport. We visit the wineries Clay suggests, and he knows the area, and The Stirling House has a great reputation in the area. That speaks volumes about the place. We go out to Lo Island Wine Country about twice a year, and only stay at Clay's inn. It is very romantic, and simply the best
Chris DiPrima

My ratings for this property      
BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (1 votes)
InnSide Tip - Reservations
Let Clay make the reservations for you. He knows everybody, and can get you in. It is so nice to not have to worry about that part of the trip. There is also a wine tour the hotel offers. It is. A great deal.
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

At A Glance

3 Review(s)
100% would stay again
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Very Good




Other Ratings: "5 Mobil Stars, "iLoveInns Guests

Publicity and Press Reviews

Coastal Living (September 2007 - chosen as one of the top five waterfront wine destinations in North America), New York Daily News, Wine Enthusiast, Well Wed, Pulse, Edible East End, Vox, Forbes 2011 selected The Stirling House for its cover story on Yahoo, and Forbes online article, News 12 Long Island, Toni On (WPIX), The Today Show (CBS)
The host, Clay can be spotted on Damages, The Good Wife, Prime Suspect, Rescue Me, The Dark Knight Rises, Gambling on Gambling, WOR radio, The host Clay can be spotted in The Romantics, The Adjustment Bureau, Batman (2012).


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