Photo by Kate Persad

Old Greenwich holiday lettings

We found 346 holiday rentals — enter your dates for availability

Discover a selection of 16 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.

Holiday rentals with weekly discounts - Old Greenwich

Showing deals for:10 Oct - 17 Oct

Why visit Old Greenwich

  • Stunning Beaches: Enjoy the beautiful coastline and sandy shores, perfect for sunbathing and family outings.
  • Scenic Parks: Discover vibrant urban parks offering a range of outdoor activities and picturesque walking paths.
  • Charming Neighbourhoods: Stroll through inviting streets filled with friendly locals and delightful shops.
  • Family-Friendly Activities: Engage in numerous activities suitable for all ages, ensuring fun for everyone.
  • Variety of Accommodations: Choose from an array of rental options, including apartments and vacation homes for a comfortable stay.

Popular types of accommodation in Old Greenwich

If you're considering a getaway to Old Greenwich, you'll find a delightful array of accommodation options to suit your needs. Our most sought-after choices include apartments, houses, and condos. Whether you're looking to rent in Old Greenwich or explore various home rentals, our platform provides you with all the information you need on rental properties in Greenwich, ensuring a hassle-free and enjoyable stay.

  • Apartments: The leading choice for holidaymakers in Old Greenwich, offering a comfortable and convenient stay with all necessary amenities.
  • Houses: A popular option for those seeking a home away from home, perfect for families or groups looking for space and privacy.
  • Condos: Ideal for those who enjoy modern living, these self-contained units provide a great blend of comfort and luxury.
  • Cottages: Quaint and charming, these properties offer a cosy retreat amidst picturesque surroundings.
  • Villas: For a touch of elegance, villas provide a luxurious holiday experience with ample space and upscale amenities.**

Top attractions in and around Old Greenwich

Old Greenwich is perfect for family-friendly, outdoor adventures and city-themed getaways. Explore its stunning beaches, vibrant urban parks, and modern colleges that offer a blend of culture and leisure. Whether you're travelling with family or seeking outdoor experiences, there's something for everyone to enjoy in this charming area of Connecticut.

  • Greenwich Avenue: A vibrant street located 1.9km from Old Greenwich, offering a delightful mix of shops, cafés, and restaurants, perfect for leisurely strolls and urban exploration.
  • Rye Playland: Situated 4.3km away, this amusement park features thrilling rides and attractions, making it an ideal destination for family outings and adventure seekers.
  • Greenwich Point Park: Nestled within Old Greenwich, this urban park boasts scenic views, picnic areas, and walking trails, perfect for family gatherings and enjoying the great outdoors.

Things to do recommended for couples

For a romantic getaway in Old Greenwich, indulge in a rejuvenating treatment at Hand & Stone Massage and Facial Spa, only 1.9km away. Enjoy lively performances at Levitt Pavilion or Tarrytown Music Hall, both providing delightful entertainment vibes for couples seeking a memorable experience.

Things to do recommended for families

During your family holiday in Old Greenwich, explore the energetic atmosphere at Chelsea Piers, unwind at the peaceful Waveny Park, and embark on an adventurous day at Legoland Discovery Center Westchester. These experiences promise fun and enjoyment for the entire family!

Things to do recommended for groups

Explore the Stamford Town Center for a delightful shopping experience, enjoy a show at the Capitol Theatre for a taste of local culture, or tee off at the Westchester Country Club for a day of sports and outdoor fun, all within a short drive from Old Greenwich.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Old Greenwich

Old Greenwich, Connecticut, offers a delightful blend of family-friendly activities and charming neighbourhoods. Visitors can explore scenic parks, the picturesque coastline, and a vibrant community atmosphere. Nearby, the town of Greenwich boasts romantic spots and relaxing venues, perfect for a leisurely stroll or a family outing. With welcoming locals and a variety of experiences, Old Greenwich is an ideal destination for a memorable holiday.

  • Riverside: Riverside is a charming city located a mere mile from Old Greenwich, offering a delightful blend of family-friendly activities and outdoor pursuits. Visitors are drawn to its vibrant shopping areas and theatres, making it an ideal spot for a day out. The proximity to beautiful local landmarks, including serene beaches and tranquil lakes, enhances the travel experience. Riverside’s access to a variety of venues ensures that there is something for everyone, making it a perfect destination for those looking to enjoy a city-themed holiday.
  • Strickland Road Historic District: This picturesque village is situated 1.2km from Old Greenwich and is renowned for its family-oriented and romantic atmosphere. Strickland Road Historic District invites travellers to explore its charming neighbourhoods and enjoy the local amusement park. With a family beach and lovely esplanade nearby, visitors can indulge in outdoor activities while soaking up the area’s historical charm. This district is perfect for a leisurely day out with loved ones, where one can relax and enjoy the scenic beauty.
  • Stamford: Located 1.2km from Old Greenwich, Stamford is a bustling city that offers a plethora of family-friendly and outdoor experiences. Its vibrant shopping areas and theatres cater to those seeking an entertaining urban experience. With local landmarks such as a lively tourist precinct and modern squares, Stamford is an excellent choice for visitors looking to immerse themselves in city life. The dynamic atmosphere and diverse attractions make it a must-visit destination during your vacation.

Best time to go to Old Greenwich

If you're planning a trip to Old Greenwich, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from May to July, while off-peak times, like October and December to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.0°F (0.0°C)Light RainMostly SunnySlightly LowSlightly Low
February33.3°F (0.7°C)Light RainMostly SunnyAverageSlightly Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageSlightly Low
April49.8°F (9.9°C)Light RainMostly SunnyAverageAverage
May59.7°F (15.4°C)Light RainMostly SunnySlightly HighAverage
June68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
July75.7°F (24.3°C)Light RainMostly SunnySlightly HighSlightly High
August74.7°F (23.7°C)Light RainMostly SunnyAverageSlightly High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October57.9°F (14.4°C)Light RainMostly SunnySlightly LowAverage
November46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
December38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly High

What do I need to keep in mind when booking a vacation in 'Old Greenwich

When travelling with a group, family, pets, or seeking extended stays, it’s important to prioritise your preferences when filtering options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Old Greenwich with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Old Greenwich with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Old Greenwich: For many families, a holiday wouldn’t be the same without their furry companion joining in. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Old Greenwich: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume your previous arrangements, or keep track of your itineraries. You can easily find the properties you’ve saved or booked, organised into sections for Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • Cummings Park Beach (2.7 mi / 4.3 km)
  • Cove Island Park (3.7 mi / 6 km)
  • Hawthorne Beach (5.4 mi / 8.7 km)
  • Caumsett State Historic Park Preserve (8.7 mi / 14 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 rental accommodation in Old Greenwich?
According to our research, houses are considered the most popular holiday rental type in Old Greenwich. But that goes without saying, everyone's idea of an epic stay isn't going to be the same. Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo and the number of guests to see your rental 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 rentals in Old Greenwich?
Yes. You can pick from nine holiday rentals that allow pets in Old Greenwich. Plenty of our pet-friendly holiday rentals 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 Vrbo.
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 Vrbo. Morning swim, sunset soak or midnight dip? Leisure time is your call when your holiday property has a swimming pool.
What are popular rental amenities in Old Greenwich?
An electric car charging station, a nearby waterfront and a fireplace are rated the most popular rental amenities in Old Greenwich. Whether you're heading away by yourself, with your other half or a group of family members, Vrbo will help you find a holiday home that matches your tastes with all the extras you're looking for.
Are there large group holiday rentals 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 rentals 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 rentals. 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 rentals with WiFi in Old Greenwich?
You can pick from two holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Old Greenwich?
Work out your travel dates and then use our filter tool to see holiday rentals with ac in Old Greenwich on Vrbo. 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 rental in Old Greenwich?
The minimum required age is usually 16, 18 or 21. It can differ from one property to another on Vrbo, so look at the rules of your preferred Old Greenwich holiday rental before making a booking.
How long can I rent a holiday rental in Old Greenwich for?
The amount of time you can book an Old Greenwich holiday rental 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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