Photo by Kate Persad

Old Greenwich holiday rentals

We found 334 holiday rentals — enter your dates for availability

Discover a selection of 14 homes and other holiday rentals in Old Greenwich that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Friendly Old Greenwich will entice you

The beaches and other outdoor surroundings create an inviting atmosphere in Old Greenwich. This welcoming and romantic city entices travellers with its restaurants and shopping. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Old Greenwich

Are you looking for top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Old Greenwich a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Chelsea Piers (3.3 mi / 5.4 km)
  • Rye Playland (6.9 mi / 11.1 km)
  • Bayville Adventure Park (8 mi / 12.9 km)
  • Norwalk Maritime Aquarium (9.4 mi / 15.1 km)
  • Cold Spring Harbor Laboratory (12.3 mi / 19.9 km)
  • Harbor Links Golf Course (14.7 mi / 23.7 km)

Exploring the natural landscape of Old Greenwich

Whether you're looking for adventure or just want to spend some time taking in the scenery, Old Greenwich is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Greenwich Point Park (1.6 mi / 2.6 km)
  • West Beach (2.5 mi / 4 km)
  • Cove Island Park (3.7 mi / 6 km)
  • Calf Pasture Beach (10 mi / 16.1 km)
  • Theodore Roosevelt Memorial Park (10.3 mi / 16.6 km)
  • Planting Fields Arboretum State Historic Park (11.1 mi / 17.9 km)

Transport options to and around Old Greenwich

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 7.9 mi (12.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Farmingdale, NY (FRG-Republic), which is 21.6 mi (34.7 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Old Greenwich?
According to our research, houses are considered the most popular holiday home type in Old Greenwich. But that goes without saying, everyone’s idea of an epic stay isn’t going to be the same. Stayz has holiday homes of all shapes and sizes, so you’re sure to find the best fit for your needs.
How much does it cost to rent a holiday home in Old Greenwich?
Length of stay, season and property type are among the factors that can affect the price of a holiday home. Simply add your travel dates to find your perfect escape. From cosy country cottages to expansive luxury villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Old Greenwich?
Prices for beach houses in Old Greenwich differ depending on the style and size of the property and when you plan to travel. All you need to do is enter your travel dates into Stayz and the number of guests to see your home options and prices. From there you can use the filters to tailor your search results by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday homes in Old Greenwich?
Yes. You can pick from nine holiday homes that allow pets in Old Greenwich. Plenty of our pet-friendly holiday homes come with a garden for your furry pal to run around in, complimentary treats, special dog beds and proximity to parks and green space. Apply the “Pets allowed” filter to find your place on Stayz.
Can I rent a house with a pool in Old Greenwich?
Tick the “pool” box in our filter tool and select from three houses with private pools in Old Greenwich on Stayz. Morning swim, sunset soak or midnight dip? Leisure time is your call when your holiday property has a swimming pool.
What are popular home amenities in Old Greenwich?
An electric car charging station, a nearby waterfront and a fireplace are rated the most popular home amenities in Old Greenwich. Whether you’re heading away by yourself, with your other half or a group of family members, Stayz will help you find a holiday home that matches your tastes with all the extras you’re looking for.
Are there large group holiday homes in Old Greenwich?
Old Greenwich has three holiday homes that can accommodate 10 or more guests. These stays come with the space you need to enjoy good times with friends and family.
Are there holiday homes in Old Greenwich that welcome kids?
Bring the entire family together for fun-filled adventures in Old Greenwich at one of our nine family-friendly holiday homes. Many of these stays come with conveniences that are just perfect for getaways with children, including full kitchens, bunk beds and patios. Simply check the “Properties good for families” filter and choose your favourite.
What are the top attractions for families in Old Greenwich?
Keeping the kids amused during your Old Greenwich holiday is simple with these top family-friendly attractions:

  • West Beach
  • Hawthorne Beach
  • Stamford Historical Society Museum

Are there holiday homes with WiFi in Old Greenwich?
You can pick from two holiday homes with WiFi in Old Greenwich. If you’d like to disconnect from daily life on your escape, but still need to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Old Greenwich?
Work out your travel dates and then use our filter tool to see holiday homes with ac in Old Greenwich on Stayz. With eight air-conditioned properties to choose from here, you can enjoy a cool and comfortable break.
How old do you have to be to rent a holiday home in Old Greenwich?
The minimum required age is usually 16, 18 or 21. It can differ from one property to another on Stayz, so look at the rules of your preferred Old Greenwich holiday home before making a booking.
How long can I rent a holiday home in Old Greenwich for?
The amount of time you can book an Old Greenwich holiday home for differs depending on the property. Simply tap in your dates of travel to view options that offer long-term stays. They come with the things you need to make your extended trip more enjoyable such as kitchens and air conditioning. Some holiday homes might also offer weekly or monthly discounts, so you can hang around longer for less.

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