Old Greenwich holiday rentals

We found 342 holiday rentals — enter your dates for availability
Discover a selection of 13 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:25 Dec - 1 Jan

Interior
Private kitchen
Dining
Room
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
AU$8,861
for 7 nights, 1 home
AU$1,266 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Private kitchen
Children’s area
Private kitchen
Children’s area
Exceptional
(25 reviews)

Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.

Greenwich

8% off
AU$4,540
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.
Outdoor dining
Marina
Interior
Exterior
Wonderful
(16 reviews)

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Stamford

7% off
AU$2,112
for 7 nights, 1 apartment
AU$302 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Living area
Private kitchen
Private kitchen
Interior
Exceptional
(17 reviews)

Downtown One Bedroom Suite Steps to Metro North

Harrison

16% off
AU$2,642
for 7 nights, 1 apartment
AU$377 per night
includes taxes & fees
Downtown One Bedroom Suite Steps to Metro North
Living area
Living area
Dining
Room
Very good
(13 reviews)

❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC

Stamford

7% off
AU$2,238
for 7 nights, 1 apartment
AU$320 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Private kitchen
Interior
Room
Interior
Exceptional
(10 reviews)

The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Stamford

5% off
AU$1,425
for 7 nights, 1 apartment
AU$204 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

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    Enjoy full kitchens, laundry, pools, gardens and more

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    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)
  • Glen Island Harbour Club (14.6 mi / 23.5 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)
  • Hawthorne Beach (5.4 mi / 8.7 km)
  • Rye Beach (7.1 mi / 11.5 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

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.
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 Stayz.
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.
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.
Are all fees included in the Old Greenwich holiday homes prices shown on Stayz?
Stayz 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.
Are there any Old Greenwich holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Old Greenwich holiday homes?
You can find great discounts on holiday homes in Old Greenwich on Stayz, 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.
Can I change or cancel my Old Greenwich holiday home booking on Stayz?
To find Old Greenwich holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Old Greenwich?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Old Greenwich holiday home?
Book your Old Greenwich holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old Greenwich?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Old Greenwich to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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