We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Stirling House Bed and Breakfast

Show Prices
Certificate of Excellence
Book on TripAdvisor
Trusted partner. We work with to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Enter dates for best prices
powered by PriceFinder
1 room
Check In Check Out
Please enter your travel dates to continue
Check Availability
Compare best prices from top travel sites
and 5 more sites!
Professional photos
Stirling House Bed and Breakfast
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"containerClass":null,"scriptFlags":null}
Add Photo Write a Review

245 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
There are newer reviews for Stirling House Bed and Breakfast
See the most recent reviews
Showing 243: English reviews
Alexandria, Virginia
Level Contributor
30 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 32 helpful votes
Reviewed 3 September 2010

I echo the positive comments of reviewers that this B&B is exceptional because it has so much going for it. In real estate, they say there are 3 things that are important to consider when you buy a home: location, location, and of course location. Stirling House has this one well-covered as you are situated at the end of a... More 

1 Thank BuerreBrr
Harbeson, Delaware
Level Contributor
10 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
Reviewed 2 September 2010

After reading all the outstanding reviews of The Stirling B & B I decided to surprise my husband with a stay there for his birthday. The price seemed high, at $300/nt for Mon & Tue stay, but I figured there was great value according to all the reviews so I was happy to pay it. We stayed in the Shelter... More 

3 Thank Enjoylife927
staten island
1 review
Reviewed 1 September 2010

The host was very accomidating his breakfasts were excellent. The bed and breakfast living and sleeping areas are very clean and nicely decorated.

Thank restypag
East Northport
1 review
Reviewed 28 August 2010

Staying at Stirling House is like staying at a good friend's place, except you don't have to offer to help with chores; also, your friend has great taste and prepares inventive and delicious breakfasts! Our room was filled with personal touches and felt more like a home than a hotel. Clay, the owner, is extremely knowledgeable about the area (think... More 

Thank spenny25k
1 review
Reviewed 18 August 2010

The place is very nice and clean. Clay is a warm friendly host and an excellent cook. He baked cookies and offered them during the day. The breakfast was wonderful too! We had a wonderful time.

Thank kathrynjoan1949
Level Contributor
15 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
Reviewed 10 August 2010

Even though we didn't have the pleasure of meeting Clay, Chris was very nice and helpful. The B&B itself was beautiful! The room was huge and lovely. We traveled for my husband's class reunion in Southampton, and it was only a 40 min drive. We have never been to Greenport and fell in love with it instantly! Everything was in... More 

Thank Mommyof3luvs
Madison, Wisconsin
1 review
Reviewed 25 July 2010

Stirling House Bed and Breakfast is top-notch in every possible way. The setting is beautiful, the guest rooms gorgeous and comfortable, and the food outstanding. Clay goes out of his way to make you feel at home. His exquisite touch is evident everywhere. I would rank this as the best bed and breakfast experience I've ever had, bar none. What... More 

Thank MadcityDon
1 review
Reviewed 22 July 2010

From the moment we arrived, our stay at the Stirling House was perfect. Our host Clay met us at the door with a warm welcome. The room was clean, comfortable and just right for our needs. An afternoon on the porch is highly recommended. It is the perfect place to relax and enjoy the view of Shelter Island. Breakfast was... More 

Thank Menemsha-10
Brooklyn, New York
1 review
Reviewed 22 July 2010

My husband and I had a wonderful weekend at the Stirling House. It was clean, comfortable, and beautifully decorated. It is within walking distance of all there is to see in Greenport but tucked away at the end of a quiet and charming block. Clay prepares the most delicious breakfasts, which you enjoy on the porch while watching the boats... More 

Thank Tricia113
1 review
Reviewed 21 July 2010

I have stayed at the Stirling House several times and I plan to do so several more! It gives you all the comforts of home with that great "vacation getaway feeling!" Clay is an amazing host, and not to mention an exceptional chef! I would highly recommend the Stirling House B&B to everyone!

Thank DLE5677

108 photos of this hotel

Traveller photos: See what travellers like you saw

All Traveller Photos (80)
Hotel & Grounds (14)
Dining (12)
Room/Suite (13)
View from Room (2)
Videos (2)
Other (37)

Management photos: Courtesy of the property manager

All Management Photos (28)
View from Room (8)
Bathroom (3)
Room/Suite (7)
Dining (1)
Business Centre/Function Rooms (1)
Hotel & Grounds (4)
Other (4)
Check In Check Out
Hotels you might also like...
Also consider these accommodations in or near Greenport
0.6 km away
Harborfront Inn at Greenport
3.4 km away
Sound View Inn
Sound View Inn
#2 of 7 in Greenport
459 reviews
2.8 km away
Cliffside Resort Condominiums
Show Prices
Show Prices
Show Prices
2.5 km away
The Blue Inn At North Fork
The Blue Inn At North Fork
#1 of 1 in East Marion
171 reviews
3.6 km away
Shelter Island House
Shelter Island House
#1 of 5 in Shelter Island
60 reviews
0.8 km away
Fordham House
Fordham House
#1 of 10 in Greenport
182 reviews
Show Prices
Show Prices
Show Prices


  • Free High Speed Internet ( WiFi )
  • Free Breakfast
  • Beachfront
  • Free Parking
  • Bar/Lounge
About the property
  • Non-Smoking Hotel
  • Beachfront
Things to do
  • Bar/Lounge
Room types
  • Non-Smoking Rooms
In your room
  • Air Conditioning
  • Free Internet
  • Free High Speed Internet ( WiFi )
  • Public Wifi
  • Free Breakfast
  • Multilingual Staff
  • Free Parking
  • Concierge
Official Description (provided by the hotel)
Waterfront luxury in Greenport Village. Thank you to our guests! June, 2015 - Tripadvisor inducted The Stirling House into its Hall of Fame for receiving the Award of Excellence for the fifth year in a row. Featured on NBC's The Today Show, The Stirling House Bed & Breakfast is the top rated waterfront inn of Long Island. Quality abounds and the guests come first at The Stirling House, Long Island Wine Country's gem. Award winning breakfasts, gorgeous views of Greenport Harbor and Shelter. Boutique hotel, with expert concierge service. Vine Time, the total wine experience is both hosted by The Stirling House. Licensed by NYS Liquor Authority, The Stirling House is the North Fork's ONLY fully wine licensed B&B. 06/2011 Vine University - The All inclusive wine making class and getaway has started and has been met with very favorable reviews from their "freshman class". Stirling House provides their guests with complimentary area beach passes, as well as towels and chairs on demand. Wi-fi, i-Pod docking stations, ensuite pruvate bathrooms, flatscreen TV/DVD players, fireplaces, and so much more. You will never want to leave the porch! Better Homes and Gardens, Wine Enthusiast, Frommers, NY Daily News, WPIX TV, Edible Magazines, and Coastal Living rate The Stirling House B&B as their first choice. Shouldn't you? Celebrities come here to feel normal, and normal people are treated like celebrities. Coming Fall 2015 Guided Bike Tours of the North Fork Coming Winter 2015 Clay's Baking Lab 101 ... more   less 

Additional Information about Stirling House Bed and Breakfast

Address: 104 Bay Ave, Greenport, NY 11944-1404
Region: United States > New York > Long Island > North Fork > Greenport
Price Range: $391 - $524 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — Stirling House Bed and Breakfast 3.5*
Number of rooms: 3
Reservation Options:
TripAdvisor is proud to partner with Orbitz, Expedia, Booking.com, Priceline, Hotels.com, Agoda, Odigeo and Travelocity so you can book your Stirling House Bed and Breakfast reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
Also Known As:
Stirling House Hotel Greenport
Stirling House b&b
Stirling House Bed And Breakfast Greenport, NY - Long Island
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.
Claim Your Listing

Questions & Answers

Here's what travellers have asked, with answers from Stirling House Bed and Breakfast staff and other travellers.
2 questions
Ask a question
New York
over a year ago

See all questions (2)

Questions? Get answers from Stirling House Bed and Breakfast staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travellers prefer

“There a nice view from the Shelter Island room.”
 of 5 bubbles Gloria1201, 31 Aug 2016 | Read review
“Greenport room is quite nice”
 of 5 bubbles paull918, 18 Jul 2016 | Read review
“Beautiful and comfortable no matter what room you stay in.”
 of 5 bubbles kristinm832, 30 Dec 2015 | Read review
“The Shelter Island Room has a wonderful view!”
 of 5 bubbles aaronsQ7623GQ, 10 Nov 2015 | Read review
“Amazing water views from the Shelter Island Room!!”
 of 5 bubbles Suzybl55, 8 Jul 2015 | Read review
5 of 5
Enter dates for best prices
Check In Check Out
Price Your Stay