Discover a selection of 137 vacation rentals in Old Greenwich, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $447 per night, and houses and condos are popular options for a stay in Old Greenwich. Either way, you'll find a rental for everyone's needs.
Destination guide

The beachside setting of Old Greenwich is ready to explore

The beaches and surrounding scenery provide a peaceful ambiance to your vacation home in Old Greenwich. This welcoming and romantic city entices travelers with its restaurants and shopping. Chelsea Piers and Capitol Theatre are just a couple of the must-sees in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.


Activities and attractions in and around Old Greenwich

Do you want to discover attractions to visit while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Old Greenwich a one-of-a-kind vacation spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • E. Gaynor Brennan Golf Course (2.6 mi / 4.2 km)
  • Chelsea Piers (3.6 mi / 5.8 km)
  • Sterling Farms Golf Course (6.2 mi / 10.1 km)
  • Rye Playland (6.7 mi / 10.7 km)
  • Stanwich Club (7.8 mi / 12.6 km)
  • Bayville Adventure Park (7.8 mi / 12.6 km)
Natural features

Exploring the natural features in Old Greenwich

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Old Greenwich. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Greenwich Point Park (0.9 mi / 1.5 km)
  • Cummings Park (3 mi / 4.8 km)
  • Cove Island Park (4 mi / 6.5 km)
  • Fort Stamford Park (4.4 mi / 7.1 km)
  • McGuane Field (5.4 mi / 8.7 km)
  • Bartlett Arboretum (7.8 mi / 12.5 km)
How to get there

Transportation to and around Old Greenwich

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 7.7 mi (12.4 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Farmingdale, NY (FRG-Republic), which is 21.5 mi (34.7 km) away.

How many vacation rentals are available around Old Greenwich, CT?

Our 2020 property listings offer a large selection of 137 vacation rentals around Old Greenwich. From 98 house rentals to 22 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a beach property in Old Greenwich?

Rising in the morning to remarkable ocean vistas and the tidal roar of waves crashing on the shore. This is the stuff vacation dreams are made of! Fortunately, there are 19 beachside vacation homes to cast yourself away to. Open to other ideas? Vrbo has loads of other options to check out, including:

  • 14 seaside vacation rentals.
  • 14 village vacation rentals.
  • 12 water-view vacation rentals.

Can I rent a house in Old Greenwich?

If you want an authentic vacation experience and love having lots of space to spread out, renting an entire house is the way to go. There are 74 options listed on Vrbo. Prices begin at $95 per night. Or perhaps you'd rather choose one of the area's other popular rental options, such as:

  • Hotel: 24 vacation homes. Prices start from $99 per night.
  • Apartment: 13 vacation homes. Prices start from $130 per night.
  • Townhome: 5 vacation homes. Prices start from $226 per night.

Can I stay in Old Greenwich in a large group?

Whether you're embarking on a special getaway with the family or spending a few nights away with all your old school friends, it's always stacks of fun staying in a new place together! And the best news is that Vrbo has options to suit you. Why not take a peek at the 14 house vacation homes available here? They're the most popular option for large groups of guests. The vacation properties that are perfect for large numbers in this area include:

  • Are you looking for vacation homes that can house 6 vacationers? We have 19 that will fit the bill. Prices begin from just $132 per night.
  • If you have 8 in your crew, you'll be delighted to find out that there are 18 vacation homes perfect. You can book one for as little as $199 a night.
  • Traveling with a group of 5? We have 9 vacation homes that will meet your needs. Prices begin at just $117 a night.

So don't fret! When you book with us you can bring your dad, your cousin and all your mates to Old Greenwich.

Where are the cheapest rentals in Old Greenwich?

Vrbo is here to help you make memories with the people you hold dear. With heaps of value-for-money rentals, you're sure to stumble upon a cozy lodging to suit everyone's tastes. Cove - East Side - Shippan is a terrific area to have a look at if you want to keep your budget under control. Vrbo has 5 rentals, and the average price is an agreeable $169 per night. East Norwalk is another good option. We've got 8 rentals here, and the average price is around $195 per night.

Explore destinations around Old Greenwich