A calm lake with reflections of trees and a stone structure on the right.

Old Greenwich Vacations from $318

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Your Old Greenwich Vacation

The stress-free way to experience this lively city is with a custom-made Old Greenwich vacation package. Stay in the neighborhood of Downtown Stamford, which is great for history, bars and pubs and dining or choose someplace else — our packages are all about you. If your trip to Old Greenwich includes a little sightseeing, hit up much-loved attractions like Chelsea Piers, Greenwich Avenue and Stamford Town Center. A few clicks is all it takes to put together the perfect Old Greenwich vacation on Expedia.

The Latest Old Greenwich Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A restaurant with booths and tables, a ceiling fan, and a brick archway.
    Feb 4 - Feb 8

    Red Carpet Inn + Flight

    Cove - East Side - Shippan
    4 nights
    2.0 star property
    7.0/10 - Good (1,071 reviews)
    Roundtrip • Houston (HOU) - White Plains (HPN)
    IAH - JFK • Nonstop LGA - IAH • 1 stop
    $379
    $318
    per traveler
    found 1 day ago
    Red Carpet Inn
  • A Marriott hotel with a modern facade, multiple floors, and a covered entrance area.
    Dec 30 - Jan 4

    Stamford Marriott + Flight

    Downtown Stamford
    5 nights
    3.5 star property
    8.0/10 - Very good (1,000 reviews)
    Roundtrip • Dallas (DFW) - White Plains (HPN)
    DFW - LGA • Nonstop LGA - DFW • 1 stop
    $992
    $818
    per traveler
    found 1 day ago
    Stamford Marriott
  • An outdoor seating area with wicker furniture and a pergola overhead.
    Dec 17 - Dec 20

    Delamar Greenwich Harbor + Flight

    Greenwich
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Staff are very friendly. Beautiful, clean rooms. Delicious restaurant downstairs"
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - White Plains (HPN)
    ATL - HPN • 1 stop HPN - ATL • 1 stop
    $1,237
    $1,019
    per traveler
    found 1 day ago
    Delamar Greenwich Harbor
  • A spacious living area with a large potted plant, a sofa, a chair, and a hanging lamp.
    Dec 28 - Jan 3

    Hilton Garden Inn Norwalk + Flight

    Cranbury
    6 nights
    3.0 star property
    8.2/10 - Very good (1,007 reviews)
    "I bought the breakfast and it was not good. I think for the price, it should have been better, including better offerings. They show a picture of breakfast in the elevator but don't actually offer that during breakfast time."
    Reviewed November 11, 2026
    Roundtrip • Atlanta (ATL) - White Plains (HPN)
    ATL - EWR • Nonstop EWR - ATL • Nonstop
    $1,104
    $925
    per traveler
    found 1 day ago
    Hilton Garden Inn Norwalk
  • A checkered floor, a potted plant, and two metal ladders in a room with large windows.
    Feb 4 - Feb 8

    West Gate Inn Nyack + Flight

    Nyack
    4 nights
    3.0 star property
    7.4/10 - Good (1,521 reviews)
    Roundtrip • Houston (HOU) - White Plains (HPN)
    IAH - JFK • Nonstop LGA - IAH • 1 stop
    $445
    $379
    per traveler
    found 1 day ago
    West Gate Inn Nyack

Where to stay near Old Greenwich

Old Greenwich is the perfect destination for your next getaway, blending family-friendly vibes with outdoor adventures. Explore everything downtown Greenwich has to offer, from charming shops to delightful eateries. Whether you're planning an Old Greenwich 2024 trip or a relaxing CT trip, you’ll find the ideal atmosphere for making lasting memories.
A coastal town with autumn-colored trees and houses along the shoreline.

Riverside

Discover Riverside, a welcoming destination perfectly suited for families and weekend getaway travelers who will appreciate its vibrant mix of outdoor and city experiences. With attractions like the historic Bruce Museum of Arts and Science, the lively Greenwich Avenue for shopping, and the fun-filled Rye Playland nearby, Riverside offers a delightful escape. Located about 1 mile by car from Old Greenwich, this charming city makes for an ideal choice for your next vacation, providing both relaxation and adventure.

A coastal cityscape with a prominent rocky shoreline and a clear blue sky.

Waterside

Experience the charm of Waterside, an excellent hub for travelers looking for a blend of culture and city excitement. With attractions like the historic Glass House and the lively Rye Playland nearby, there's plenty to explore. Enjoy the vibrant shopping along Greenwich Avenue or attend events at the local arena. Located about 1 mile by car from Old Greenwich, Waterside provides easy access to both leisure and business opportunities, making it a smart choice for your stay.

A sandy beach with a clear blue sky, a rocky breakwater, and trees in the background.

West Side

If you are a family traveler or on a weekend getaway, look no further than West Side, a vibrant neighborhood in Stamford, Connecticut. This area is loved for its diverse shopping, lively theater scene, and cultural venues like The Glass House and the Stamford Public Library. With attractions such as Greenwich Avenue and the modern square nearby, there's plenty to explore. West Side is about a 2-mile drive from Old Greenwich, making it a smart choice for your stay.

A cityscape with a river, modern buildings, and green spaces.

Stamford

Stamford stands out as a prime spot for travelers interested in a blend of city excitement and outdoor experiences. With its vibrant shopping area and cultural gems like The Glass House and Historic South Norwalk, visitors can immerse themselves in art and history while enjoying the lively atmosphere. Located about 2 miles by car from Old Greenwich, Stamford offers easy access to its attractions, making it a smart choice for your next vacation stay.

A marina with various boats docked, surrounded by rocky shores and a grassy area.

South End

Travelers visiting the area often choose South End, especially families and weekend getaway seekers, drawn by its vibrant atmosphere and access to outdoor activities. With attractions like Greenwich Avenue for shopping, the historic charm of South Norwalk, and the artistic allure of The Glass House, South End provides plenty of opportunities for exploration. Located about 2 miles by car from Old Greenwich, this neighborhood makes for a smart choice for your stay, combining convenience with a wealth of local experiences.

Discover the most popular places to visit in Old Greenwich

Greenwich Point Park

9.2/10 (23 reviews)
This serene coastal park offers panoramic views of Long Island Sound and walking trails through diverse habitats. Explore the historic Innis Arden estate or watch for migratory birds in this Audubon-recognized area.
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Old Greenwich Hotel Deals

A spacious atrium with a central bar, surrounded by seating areas and a circular water feature.

Hyatt Regency Greenwich

Hyatt Regency Greenwich
4.0 star property
1 mi from Old Greenwich
8.8 out of 10, Excellent, (1,214 reviews)
$203 nightly
The price is $234
Nov 22 - Nov 23
Total with taxes and fees
Hyatt Regency Greenwich
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 Old Greenwich

Frequently Asked Questions

How much does an Old Greenwich vacation package cost?

Offering great value package deals from $318 on Expedia, you'll be pleasantly surprised at how much a vacation to Old Greenwich costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Old Greenwich?

You can usually find lower rates and greater availability in January, March and December. Browse our cheap Old Greenwich vacation packages and you could land some great off-season deals.

How many days is enough for Old Greenwich?

With a well-planned itinerary, you can easily tick off the main Old Greenwich sights in a handful of days. But if you want to discover hidden spots or take day trips, think about booking your Old Greenwich vacation for longer.

How to find the best Old Greenwich package deals?

Finding a cheap Old Greenwich package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Old Greenwich package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.

Is it cheaper to book an Old Greenwich vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still get the freedom to create a personalized Old Greenwich vacation by choosing your favorite accommodation type, airline and car class.

When to book a vacation package to Old Greenwich?

If you've got your Old Greenwich travel dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for quick escapes.

Does Expedia offer Book Now, Pay Later Old Greenwich vacation packages?

Jet off on your perfect trip to Old Greenwich with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up cheap deals before they disappear.

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