Cutchogue Vacations from $308

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Your Cutchogue Vacation

With plenty of highlights as well as some hidden gems, this city is best explored with a Cutchogue vacation package. Find a place to stay in Village of Southampton, which is good for history, coastal beaches and culture. If taking in sights is part of the plan during your trip to Cutchogue, swing by leading attractions like Macari Vineyards, Raphael Winery and Pindar Vineyards. That dream Cutchogue vacation is just a few clicks away. Search accommodations, flights and more on Expedia for an adventure that's tailored just for you.

The Latest Cutchogue vacation packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $686, price is now $308 per person
$308
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Staff were wonderful. Hotel was a great experience

Reviewed on Dec 25, 2025

Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $1,691, price is now $783 per person
$783
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,173, price is now $546 per person
$546
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Nice location, friendly staff and clean!

Reviewed on Dec 30, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,804, price is now $907 per person
$907
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
Great location, room was clean, decent sized for NY (we did have the penthouse) and courteous staff.

Reviewed on Dec 28, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $1,204, price is now $613 per person
$613
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.4/10 Very Good! (147 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

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Discover the most popular places to visit in Cutchogue

Bedell Cellars

4/5(2 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.

Bedell Cellars

Peconic Bay Winery

You can enjoy a tasting or tour at Peconic Bay Winery during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches.

Peconic Bay Winery

8 Hands Farm

Enjoy an outing to 8 Hands Farm during your stay in Cutchogue.

8 Hands Farm

What to do in Cutchogue

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

$179
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
East Hampton Shops

Hamptons Private Day Trip from New York City

$1,299
per traveler
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

$1,299
per traveler
The Hamptons and Long Island Wineries Private Tour
See all activities in Cutchogue

Cutchogue Hotel Deals

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $256 total per night from Jan 5 to Jan 6
$256 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Wonderful hotel with very courteous staff, Water's Edge is top notch in every way

Reviewed on Dec 26, 2025

Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $86 total per night from Jan 1 to Jan 2
$86 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
This hotel is clean and safe. Parking was easy. Rooms are spacious. Staff was friendly. It's not overly fancy but was perfect for a reasonable price.

Reviewed on Dec 23, 2025

Pier Blue Inn Old Saybrook - Essex
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $142 total per night from Jan 22 to Jan 23
$142 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
9.4/10 Exceptional! (410 reviews)
They really take care of us! The location is great!

Reviewed on Dec 27, 2025

The Bentley Hotel Southampton
See all 4,275 properties in Cutchogue
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.

Find the Best Cutchogue Vacation Packages

Cutchogue Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
3,300
Max Temp Winter
40ºF
Max Temp Summer
75ºF
Top Sights
Coopers Beach, Wolffer Estates Vineyard and The Hamptons Beaches

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Frequently asked questions

How much does a Cutchogue vacation package cost?
You can grab a vacation package to this popular destination from $308 on Expedia. But how much your vacation to Cutchogue costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Cutchogue?
You can usually find lower rates and better availability in January, October and December. Take a look at our cheap Cutchogue vacation packages and you could get some excellent off-season deals.
How many days is enough for Cutchogue?
The ideal length for your Cutchogue vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to check out all the major attractions and explore some hidden spots along the way.
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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize 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 vacation 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?

  1. Choose your dates: What you'd like to do in Cutchogue and your favorite season will help you decide when to go.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you'll need to consider other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Cutchogue.
  3. Use Expedia's trip planning tool to discover Cutchogue: Research every aspect of your trip to Cutchogue with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Set the duration of your trip: Start by listing all the attractions you want to experience in Cutchogue. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your airfare and accommodations: After you've settled on your travel dates and duration, book the perfect Cutchogue vacation package for you.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on Cutchogue's best offerings. Find all the incredible things to do in Cutchogue with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Cutchogue vacation packages?
Jet off on your perfect escape to Cutchogue with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next paycheck — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snag great deals before they disappear.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.