Old Greenwich holiday lettings

We found 356 holiday rentals — enter your dates for availability

Discover a selection of 12 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.

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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.

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.

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

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.

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)
  • Norwalk Maritime Aquarium (9.4 mi / 15.1 km)
  • Cold Spring Harbor Laboratory (12.3 mi / 19.9 km)
  • Sportime USA (13.4 mi / 21.6 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)
  • Caumsett State Historic Park Preserve (8.7 mi / 14 km)
  • Calf Pasture Beach (10 mi / 16.1 km)
  • Theodore Roosevelt Memorial Park (10.3 mi / 16.6 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

How much does it cost to rent a holiday home in Old Greenwich?
Prices for holiday rentals in Old Greenwich vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Old Greenwich to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Old Greenwich holiday house rentals?
You can find great discounts on house rentals in Old Greenwich on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Old Greenwich?
For renting a beach house in Old Greenwich, the picturesque coastal areas along the Long Island Sound are highly recommended. The area near Greenwich Point Park is particularly appealing, offering scenic views and easy access to sandy beaches. Many properties in this vicinity provide amenities such as spacious outdoor decks, private gardens, and fully equipped kitchens, ideal for families or groups looking to enjoy a relaxing beach getaway.

Additionally, the waterfront neighbourhoods along Shore Road and the nearby Binney Park area feature charming homes that often come with amenities like outdoor showers, barbecue grills, and direct beach access. This region is superb for those seeking a tranquil environment, with opportunities for swimming, sunbathing, and picnicking by the water.

Moreover, the proximity to local shops, cafes, and recreational facilities enhances the experience for travellers. The nearby Old Greenwich Village offers a delightful selection of boutiques and eateries, making it convenient for guests to explore the local culture and cuisine.
What is the most popular type of holiday rental accomodation in Old Greenwich?
In Old Greenwich, holiday houses are the most prevalent type of holiday rental, with around 15 available throughout the area. These homes typically feature spacious living areas, multiple bedrooms, fully equipped kitchens, and often outdoor spaces such as patios or gardens, making them ideal for families or groups. Additionally, several apartments and mobile homes are also on offer, providing alternative options for travellers seeking different experiences.
Are there any family house rentals in Old Greenwich?
In Old Greenwich, Connecticut, there are several family-friendly house rentals available, providing a wonderful base for exploring the area. Many of these homes are located in charming neighbourhoods close to local parks and the picturesque coastline. Visitors can expect spacious living areas superb for family gatherings, fully equipped kitchens for preparing meals, and lovely outdoor spaces where children can play or families can enjoy al fresco dining.

Proximity to attractions such as the scenic Greenwich Point Park, with its sandy beaches and walking trails, adds to the appeal. Additionally, the vibrant downtown area is just a short drive away, offering boutique shops, cafes, and cultural experiences.
Can I rent a holiday home with a pool or hot tub in Old Greenwich?
In Old Greenwich, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque coastal town offers a serene environment, ideal for relaxation. Many properties come equipped with private pools, hot tubs, and spacious outdoor areas, superb for enjoying warm summer days or unwinding in the evenings.

Travellers can also expect amenities such as fully equipped kitchens for home-cooked meals, comfortable living spaces, and proximity to local attractions, including beautiful beaches and charming shops.
Can I find long-stay holiday rentals in Old Greenwich?
A long-stay holiday rental in Old Greenwich is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Old Greenwich?
In Old Greenwich, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. This picturesque coastal town offers a variety of holiday homes, many of which come equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, ideal for families or groups.

The area is close to various parks and green spaces, providing ample opportunities for outdoor activities with pets. For example, the nearby Greenwich Point Park is a lovely spot for walks and picnics, featuring scenic views of the Long Island Sound. Additionally, the town's charming streets are great for leisurely strolls, offering a pleasant atmosphere for both pets and their owners.
Are there any remote work holiday rentals in Old Greenwich?
In Old Greenwich, Connecticut, there are around 18 holiday rentals suitable for remote work. This charming coastal town offers a serene environment, ideal for productivity. Many properties come equipped with high-speed internet, both through third-party services and complimentary Wi-Fi, ensuring a reliable connection for work-related tasks.

Travellers can expect a variety of amenities, including comfortable workspaces, spacious living areas, and fully equipped kitchens for convenient meal preparation. The picturesque neighbourhood is also close to local parks and waterfront areas, providing opportunities for relaxation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Old Greenwich holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Old Greenwich with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Old Greenwich?
In Old Greenwich, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature decks or patios, providing a wonderful space to relax outdoors. Pet-friendly options are available, making it convenient for those travelling with furry companions. Additionally, many rentals come with fireplaces, superb for cosy evenings, and onsite parking is commonly offered, ensuring straightforward access for guests.
When is the best time to visit Old Greenwich for a holiday rental?
The best time to visit Old Greenwich for a holiday rental is during the peak season from May to July, with July being the most popular month. This vibrant period attracts families and couples eager to enjoy the charming coastal town, with plenty of opportunities for outdoor activities, relaxing at the beach, and exploring local parks.

In July, visitors can expect warm temperatures averaging around 24 to 30 degrees Celsius, making it ideal for sunbathing, swimming, and picnicking at the picturesque Greenwich Point Park. The atmosphere is lively, with various local events and festivals enhancing the experience, providing a great backdrop for those seeking a memorable summer getaway.

For those considering a more budget-friendly option, January is a quieter month to visit. While it may be colder, with temperatures typically ranging from -3 to 4 degrees Celsius, this time offers a unique opportunity to appreciate the serene beauty of Old Greenwich. You can enjoy peaceful walks along the waterfront and explore the local shops without the seasonal crowds.
How early should I book a Old Greenwich holiday rental?
Book your Old Greenwich holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Old Greenwich?
In Old Greenwich, visitors can enjoy a charming coastal experience with a variety of attractions. The picturesque Greenwich Point Park, also known as Tod's Point, offers beautiful beaches, walking trails, and stunning views of Long Island Sound, making it a popular spot for picnicking and outdoor activities. The park is an ideal place for families to relax and enjoy the scenic waterfront.

For those interested in local history, the Bruce Museum provides fascinating exhibits on art, science, and natural history. The museum is located near the town centre, where visitors can stroll through quaint streets lined with boutique shops and delightful cafes.

Additionally, the local area features several parks, such as Binney Park and the nearby Greenwich Audubon Centre, which provide excellent opportunities for nature walks and birdwatching.
Can I change or cancel my Old Greenwich home rental booking on Vrbo?
To find Old Greenwich holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Old Greenwich holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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