--- title: "Town of Southold Town Vacation Packages 2026 from $404 | Expedia" description: "Bundle your Town of Southold Town flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels ✅" canonical: "https://www.expedia.com/Town-Of-Southold-Town.d553248635976002319.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-14T05:23:23Z --- # Town of Southold Town Vacations & Trips from $404 ![A white colonial-style house with a green roof and a lighthouse tower.](https://images.trvl-media.com/place/553248635976002319/fad589d6-7ab0-42b0-86db-2d106ae76b7b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ### Top destinations in Town of Southold Town ![A pebbled beach at sunset with the sun setting over the horizon.](https://images.trvl-media.com/place/110728/52d32607-4fbb-4409-ba38-04d4ab724050.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Greenport](https://www.expedia.com/Greenport.d110728.Destination-Travel-Guides) ![A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.](https://images.trvl-media.com/place/183719/b634a311-72c8-4775-8993-a7fef52c97ee.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Southold](https://www.expedia.com/Southold.d183719.Destination-Travel-Guides) ![A pebble beach at sunset with a calm sea in the background.](https://images.trvl-media.com/place/553248635074738584/5b9a0513-04ba-43fa-b998-b43d78e2cdf1.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Mattituck](https://www.expedia.com/Mattituck.d6223780.Destination-Travel-Guides) ![A coastal landscape with a sandy beach, calm waters, and a clear sky.](https://images.trvl-media.com/place/183659/bed04c32-7dcf-488b-8b18-9bd347a20dc2.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Cutchogue](https://www.expedia.com/Cutchogue.d183659.Destination-Travel-Guides) ![An aerial view of a coastal area with a sandy beach, a small settlement, and a clear blue sea.](https://images.trvl-media.com/place/6326191/dc5cfaf6-a490-40b7-8f4c-4ee3155c69e6.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Orient](https://www.expedia.com/Orient.d6326191.Destination-Travel-Guides) ![A coastal landscape with a sandy beach, clear blue water, and a distant lighthouse.](https://images.trvl-media.com/place/183659/5b925f81-ea4b-4e7a-b93a-66611b53a810.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Greenport West](https://www.expedia.com/Greenport-West.d553248635975876381.Destination-Travel-Guides) ![A sunset over a coastal landscape with a large body of water, a sandy beach, and a forested area.](https://images.trvl-media.com/place/144477/65f617d0-d0a2-4896-9c6d-c9a69f4bfc0b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Peconic](https://www.expedia.com/Peconic.d144477.Destination-Travel-Guides) ![A coastal landscape with a sandy beach, calm water, and scattered trees.](https://images.trvl-media.com/place/6069914/91e6a04d-cea0-4ca3-a467-cb23f6c7ba9f.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [East Marion](https://www.expedia.com/East-Marion.d6069914.Destination-Travel-Guides) ![A roadside signboard advertising fresh local produce and farm fresh berries.](https://images.trvl-media.com/place/6323751/f443a972-0a35-4a0a-928d-ee101685ef10.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### [Laurel](https://www.expedia.com/Laurel.d6131264.Destination-Travel-Guides) ## The Latest Town of Southold Town Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A rooftop terrace with two lounge chairs, a small table, and a sofa. A green hedge and a metal railing are visible. In the background, a large suspension bridge and a construction crane are seen.](https://images.trvl-media.com/lodging/21000000/20870000/20868200/20868143/6b870d38.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A bar area with wooden bar stools, a well-stocked shelf with bottles, and a large window providing a view outside.](https://images.trvl-media.com/lodging/21000000/20870000/20868200/20868143/5678956a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 28 - Jan 31** ### [33 Hotel, New York City, Seaport + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-28/2027-01-31/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20868143&dealMarker=&paandie=true&cabinClass=e) Manhattan 3 nights **9.0/10** \- Wonderful (1,001 reviews) Roundtrip • Atlanta (ATL) - New York (JFK) ATL - LGA • Nonstop LGA - ATL • Nonstop [~~$634~~](https://www.expedia.com/) **$404** per traveler found 1 day ago - ![A rooftop terrace with outdoor seating, a city view, and a brick building.](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/9118c9d6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A restaurant with booths and tables, warm lighting, and a view of the bar area.](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/92dcb0b0.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 7 - Jan 10** ### [JW Marriott Essex House New York + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-07/2027-01-10/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=534143&dealMarker=&paandie=true&cabinClass=e) Manhattan 3 nights **8.8/10** \- Excellent (1,001 reviews) Roundtrip • Atlanta (ATL) - New York (JFK) ATL - LGA • Nonstop EWR - ATL • Nonstop [~~$1,448~~](https://www.expedia.com/) **$731** per traveler found 1 day ago - ![A historic building with ornate architectural details, multiple floors, and illuminated windows.](https://images.trvl-media.com/lodging/1000000/10000/6400/6365/23f19baf.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern room with a large window, a grey sofa, and a decorative ball.](https://images.trvl-media.com/lodging/1000000/10000/6400/6365/0a3b7c6d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 15 - Jan 20** ### [The St. Regis New York + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-15/2027-01-20/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6365&dealMarker=&paandie=true&cabinClass=e) Manhattan 5 nights **9.2/10** \- Wonderful (295 reviews) "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong" Reviewed November 6, 2026 Roundtrip • Atlanta (ATL) - New York (JFK) ATL - JFK • Nonstop JFK - ATL • Nonstop Save 100% on your flight [~~$3,565~~](https://www.expedia.com/) **$2,117** per traveler found 1 day ago - ![A rooftop terrace with a city skyline view, blue seating, and potted plants.](https://images.trvl-media.com/lodging/67000000/66530000/66525900/66525849/4e36b4c5.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A large indoor statue of the Statue of Liberty holding a globe, surrounded by dining tables and chairs, with a ceiling that features a sky and cloud design.](https://images.trvl-media.com/lodging/67000000/66530000/66525900/66525849/3f3ed867.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 16 - Jan 19** ### [Margaritaville Resort Times Square + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-19/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=66525849&dealMarker=&paandie=true&cabinClass=e) Manhattan 3 nights **9.0/10** \- Wonderful (4,134 reviews) "Great location and check in was simple. Walkable to lots and Times Square. Restaurants and bars are great but cannot charge to your room so that was a pain if you want to do that. Check out was the only issue. Check out was at 12 and we decided to get breakfast first. Got back to room aroud 11:40 and room key no longer worked. They shut it off. Had to go do lobby and wait in line to get it turned back on which was a bit stressful. Others had the same thing happen to them so I would watch out for..." Reviewed November 13, 2026 Roundtrip • Atlanta (ATL) - New York (JFK) ATL - LGA • Nonstop EWR - ATL • Nonstop [~~$715~~](https://www.expedia.com/) **$453** per traveler found 1 day ago - ![A tall building with a spire, adjacent to a shorter building with ornate detailing.](https://images.trvl-media.com/lodging/4000000/3630000/3630000/3629903/f11b4f1b.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern outdoor seating area with a sofa, chairs, and a table, surrounded by potted plants and a decorative fence.](https://images.trvl-media.com/lodging/4000000/3630000/3630000/3629903/dee0c7b3.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 22 - Jan 25** ### [The Langham, New York, Fifth Avenue + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-22/2027-01-25/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3629903&dealMarker=&paandie=true&cabinClass=e) Manhattan 3 nights **9.6/10** \- Exceptional (1,000 reviews) Roundtrip • Atlanta (ATL) - New York (JFK) ATL - JFK • Nonstop JFK - ATL • Nonstop [~~$1,307~~](https://www.expedia.com/) **$836** per traveler found 1 day ago ## Discover the most popular places to visit in Town of Southold Town ![Sunflowers in a field with a building in the background.](https://images.trvl-media.com/place/144477/46d31186-1a5d-467c-95f7-01cb656b92d4.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Photo by 4 Star Traveler ### Pindar Vineyards Rating: 8.4/10 (8 reviews) You can enjoy a tasting or tour at Pindar Vineyards during your travels to Peconic. Discover the area's sunsets and wineries. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326965) ### Orient Point County Park ![A rocky shoreline with large boulders and a calm sea.](https://images.trvl-media.com/place/553248621532665781/8c0db532-2fba-4077-be07-e2c6e7873246.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Rating: 10.0/10 (1 review) Explore the great outdoors at Orient Point County Park, a lovely green space in Orient Point. Stroll along the beaches or discover the area's sunsets. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665781) ![A vineyard with rows of grapevines under a partly cloudy sky.](https://images.trvl-media.com/place/144477/097a28ec-b48b-4a02-aef3-3c165612407a.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Photo by Adriana T ### Bedell Cellars Rating: 8.6/10 (4 reviews) You can enjoy a tasting or tour at Bedell Cellars during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665643) ![A street sign for New York 90.](https://images.trvl-media.com/place/6326191/c9f7d09d-14c2-4627-b456-17bc55910d0e.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium) Photo by Joe Vickiana ### Orient Beach State Park Rating: 8.6/10 (33 reviews) You can take time to visit Orient Beach State Park during your travels to Orient. Stroll along the waterfront or discover the area's sunsets. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6064487) ### Raphael Winery You can enjoy a tasting or tour at Raphael Winery during your travels to Peconic. Wander the beaches or discover the area's sunsets. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6327146) ### 67 Steps Beach Rating: 9.6/10 (26 reviews) Why not spend a carefree afternoon at 67 Steps Beach during your travels in Greenport? Take in the festivals and sunsets in the area. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248626388140598) ### Macari Vineyards Rating: 8.0/10 (1 review) You can enjoy a tasting or tour at Macari Vineyards during your travels to Mattituck. While you're in the area, stroll along the beautiful beaches. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326944) ### Harbes Family Farm Rating: 10.0/10 (2 reviews) You can search for that perfect souvenir at Harbes Family Farm during your trip to Mattituck. While you're in the area, stroll along the beautiful beaches. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6326899) ### What to do in Town of Southold Town ![Mystic Seaport Museum Adventure ](https://mediaim.expedia.com/localexpert/1127879/dee4c344-7a93-436c-8f37-9a7eee4e5869.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Mystic Seaport Museum Adventure](https://www.expedia.com/things-to-do/a.a1127879.activity-details?rid=553248635976002319) $35 per adult 92% of travelers recommend ![Mystic: Guided Ghost Tour of Downtown Mystic at Night](https://mediaim.expedia.com/localexpert/46269188/5e495bc7-e92d-4772-8daa-f22e84f17ecb.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Mystic: Guided Ghost Tour of Downtown Mystic at Night](https://www.expedia.com/things-to-do/a.a46269188.activity-details?rid=553248635976002319) $35 per adult 96% of travelers recommend ![Downtown Westerly Ghost Tour](https://mediaim.expedia.com/localexpert/46269045/d7d74544-0666-457b-b9b4-314da4ce25f3.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Downtown Westerly Ghost Tour](https://www.expedia.com/things-to-do/a.a46269045.activity-details?rid=553248635976002319) $35 per adult 100% of travelers recommend [See all activities in Town of Southold Town](https://www.expedia.com/things-to-do/search?rid=553248635976002319) ## Town of Southold Town Hotel Deals ### [Zey Hotel](https://www.expedia.com/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information) ![A two-story house with a covered patio, outdoor seating, and a well-maintained lawn.](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/5e616fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 439 Main Street, Greenport, NY, 11944, US - Location: 4.5 mi from Town of Southold Town - Star rating: 3.5/5 - Guest rating: 9.2/10 (Wonderful, 449 reviews) - Price: $143 nightly, $163 total, Dec 15 - Dec 16, Total with taxes and fees - Review: Great place to stay for a walkable visit to Greenport NY. Comfy bed, great rooms for hanging out, close to everything. ### [The Shoals Suites and Slips](https://www.expedia.com/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information) ![A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 61600 Main Rd, Southold, NY, 11971, US - Location: 1.5 mi from Town of Southold Town - Star rating: 3.5/5 - Guest rating: 9.4/10 (Exceptional, 351 reviews) - Price: $210 nightly, $237 total, Nov 29 - Nov 30, Total with taxes and fees - Review: The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing. ### [The Harbor Front Inn](https://www.expedia.com/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/27a70577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 209 Front St, Greenport, NY, 11944, US - Location: 4.3 mi from Town of Southold Town - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 676 reviews) - Price: $148 nightly, $169 total, Dec 13 - Dec 14, Total with taxes and fees - Review: Clean and comfortable room. Great location to walk around town. Nice continental breakfast. ### [Silver Sands Motel & Beach Bungalows](https://www.expedia.com/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![A beach with sun loungers and umbrellas, a sandy path, and a view of the water.](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/0f51f23c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1400 Silvermere Rd, Greenport, NY, 11944, US - Location: 3.4 mi from Town of Southold Town - Star rating: 4/5 - Guest rating: 10/10 (Exceptional, 192 reviews) - Price: $189 nightly, $216 total, Dec 15 - Dec 16, Total with taxes and fees - Review: Amazing place to stay with a great location. We will definitely be back! ### [Sound View Greenport](https://www.expedia.com/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![A spacious room with wicker furniture, large windows, and a view of the sea.](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 58775 County Rd 48, Greenport, NY, 11944, US - Location: 2.7 mi from Town of Southold Town - Star rating: 4/5 - Guest rating: 8.4/10 (Very good, 768 reviews) - Price: $174 nightly, $199 total, Dec 14 - Dec 15, Total with taxes and fees - Review: "Location is nice. But many times booked for weddings so you won’t be able to go to the bar etc. The rooms are clean and fine but for the pricing I expected nicer. Feels more like a cabin. They also have fees that are not represented on an app like Expedia if you book through them. An additional 30 for overnight parking when you are paying 600 a night for a mediocre room on Long Island in November you would expect that to be included. Overall would not stay again there are much better options.... ### [Oyster Estate](https://www.expedia.com/Greenport-Hotels-Oyster-Estate.h90308554.Hotel-Information) ![A cozy interior with a wooden bench, a sofa, and a bar area.](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/a6bc5ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 326 Front St, Greenport, NY, 11944, US - Location: 4.2 mi from Town of Southold Town - Star rating: 4/5 - Guest rating: 9.2/10 (Wonderful, 302 reviews) - Price: $211 nightly, $241 total, Dec 13 - Dec 14, Total with taxes and fees ### [The Menhaden](https://www.expedia.com/Greenport-Hotels-The-Menhaden.h35229370.Hotel-Information) ![A two-story building with large windows, a sign reading "The Menhaden," and bicycles parked outside.](https://images.trvl-media.com/lodging/36000000/35230000/35229400/35229370/a4e7f774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 207 Front St, Greenport, NY, 11944, US - Location: 4.3 mi from Town of Southold Town - Star rating: 3.5/5 - Guest rating: 9.6/10 (Exceptional, 197 reviews) - Price: $294 nightly, $336 total, Dec 14 - Dec 15, Total with taxes and fees ### [American Beech Hotel](https://www.expedia.com/Greenport-Hotels-American-Beech-Hotel.h11951124.Hotel-Information) ![A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.](https://images.trvl-media.com/lodging/12000000/11960000/11951200/11951124/81e91eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 300 Main Street, Greenport, NY, 11944, US - Location: 4.5 mi from Town of Southold Town - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 208 reviews) - Price: $274 nightly, $313 total, Nov 16 - Nov 17, Total with taxes and fees Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [See all properties in Town of Southold Town](https://www.expedia.com/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=553248635976002319&adults=2&sort=RECOMMENDED&openPlayBack=true) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/ fr-FR: https://www.expedia.fr/Town-Of-Southold-Town.d553248635976002319.Reservation-Sejours-Voyages ```