Cutchogue Holidays
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Top hotels in Cutchogue
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
S$150
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,004 reviews)
"Our unit had spider webs on the ceiling. Bed was short sheeted. We had to remake the bed ourselves. Nonexistent Wi-Fi connection. One bar. Kept disconnecting. One ice machine was working for all units. Staff was nice. Helpful. Upstairs chambermaid came down to remove the spider webs. We appreciated ..."
Reviewed on 14 Aug, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
S$496
10 Sept - 11 Sept
includes taxes & fees
8.4/10 Very good! (688 reviews)
"Not a 4 star place, just ok, no hand soap, no water glasses, pretty bare bones for a stay, but I’m sure it’s lovely to go to the property for an event or dinner maybe."
Reviewed on 14 Aug, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
S$365
14 Sept - 15 Sept
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"Nice resort, very convenient. However, a little pricey and every time you turned around there was a gratuity. Food was ok, not great for the price paid though."
Reviewed on 14 Aug, 2026
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.
Stay near popular Cutchogue attractions
Bedell Cellars
8.6/10 (4 reviews)
This award-winning Long Island winery served its 2009 Merlot at the 2013 Presidential Inauguration. Sample handcrafted wines in a renovated barn with panoramic vineyard views and artisanal cheese pairings.
8 Hands Farm
This regenerative farm showcases heritage breed animals and sustainable practices. Sample artisanal charcuterie and seasonal farm-to-plate offerings at the on-site store while exploring the pastoral landscape.
Lieb Cellars Tasting Room
You can enjoy a tasting or tour at Lieb Cellars Tasting Room during your travels to Cutchogue.
Waters Crest Winery
This family-run North Fork winery crafted distinctive Cabernet Franc and Merlot in an intimate setting. Visitors could enjoy personalised tastings with owner Jim Waters and attend enlightening "Wine University" classes.
Cutchogue Village Green
Step back in time at Cutchogue Village Green, home to the Old House (1649), one of New York State's oldest English-style dwellings. Wander through preserved colonial buildings that illuminate early American life.
Pugliese Vineyards
8.0/10 (2 reviews)
This family-owned North Fork winery offers estate-bottled varieties and sparkling champagnes in an intimate setting. Enjoy guided tastings beside a picturesque koi pond while savouring the serene vineyard atmosphere.
Pellegrini Vineyards
Pellegrini Vineyards crafts award-winning Merlot and Chardonnay in its on-site winemaking facility. Savour premium tastings in the cathedral-like tasting room with vineyard views or explore through self-guided tours.
McCall Wines
10.0/10 (1 review)
This sustainable vineyard pairs award-winning Pinot Noir with the rustic charm of a converted potato barn. Sample their acclaimed wines while watching Charolais cattle graze among the vines.
What to do in Cutchogue
The Hamptons and Long Island Wineries Private Tour
S$1,674
per traveller
Full Day Private Long Island Wine Tours from New York City
S$244
per adult
Frequently asked questions
How much does a Cutchogue holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday to Cutchogue costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Cutchogue?
If you're looking to book a cheap Cutchogue holiday package, consider planning a trip in January, February and March. You're likely to find better prices on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Cutchogue?
Generally, a handful of days is enough to check out the main attractions during your Cutchogue holiday. However, if you prefer to have time to kick back or take day tours, consider extending your trip.
How to find the best Cutchogue package deals?
Begin your search for a Cutchogue package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Cutchogue package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cutchogue adventure off to a flying start.
Is it cheaper to book a Cutchogue holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise your Cutchogue trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Cutchogue?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Cutchogue break.
How to plan a trip to Cutchogue?
- Choose when to go: Check your diary and pack your bags. Your favourite season and the activities available will also help you decide when to visit Cutchogue.
- Work out your budget: Ensure you have enough money to pay for everything from transportation and food to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Cutchogue.
- Decide your trip length: Consider how long you want to spend discovering Cutchogue. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your airfare and accommodation: Once you've nailed down your travel dates and duration, book the perfect Cutchogue holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
